Abstract
An in depth account of intramolecular 1,3-dipolar cycloadditions involving dipoles such as nitrile oxides, silyl nitronates, H-nitrones, azides, and nitrilimines is presented with particular emphasis on the stereochemistry during the cycloaddition. Various methods employed for the generation of the dipoles and their applications to stereoselective synthesis are also discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Similar content being viewed by others
7 References
a) Huisgen R (1963) Angew Chem Int Ed Engl 2:565; b) Huisgen R (1963) Angew Chem Int Ed Engl 2:633
Padwa A (ed) (1984) 1, 3-Dipolar cycloaddition chemistry. Wiley, New York
Hassner A, Murthy KSK, Maurya R, Dehaen W, Friedman O (1994) J Heterocycl Chem 31:687
Curran DP (1988) In: Curran DP (ed) Advances in cycloaddition. JAI, London, vol 1, p 129
a) Kozikowski AP (1984) Acc Chem Res 17:410; b) Oppolzer W (ed) (1985) Symposia-inprint Number 21, Tetrahedron 41:3447; c) Jäger V, Müller R, Leibold T, Hein M, Schwarz M, Fengler M, Jaroskova L, Pärzel M, Le Roy P-Y (1994) Bull Soc Chim Belg 103:491
a) LeBel NA, Whang JJ (1959) J Am Chem Soc 81:6334; b) Padwa AW (1976) Angew Chem Int Ed Engl 15:123; c) Oppolzer W (1977) Angew Chem Int Ed Engl 16:10
Brieger G, Bennett JN (1980) Chem Rev 80:63
Broggini G, Zecchi G (1999) Synthesis 905
Kamimura A (1992) Yuki Gosei Kagaku Kyokaishi 50:808
Kanemasa S, Tsuge O (1990) Heterocycles 30:719
See for example: a) Grundman C, Dean JM (1965) J Org Chem. 30:2809; b) Hassner A, Rai KML (1989) Synthesis 57
a) Mukaiyama T, Hoshino T (1960) J Am Chem Soc 82:5339; b) Basel Y, Hassner A (1997) Synthesis 309; c) see also: Shimizu T, Hayashi T, Shibafuchi H, Teramura K (1986) Bull Chem Soc Jpn 59:2827 for Et chloroformate/Et3N/DMAP method
Jung ME, Vu BT (1996) Tetrahedron Lett 37:451
a) Raposo C, Wilcox CS (1999) Tetrahedron Lett 40:1285; b) in DMSO at 150 °C; private communication; c) 6a is the minor isomer because it requires the most hindered TS where the phenyl group must circumvent the dimethylamino group; d) The disappearance of 6b has been attributed to a higher steric hindrance due to the new methyl group on the amine nitrogen and/or to electrostatic repulsion attending non-favorable approach of the dipole in the presence of the charge
Huisgen R (1988) In: Curran DP (ed) Advances in cycloaddition. Jay Press, London, vol 1, p 1
a) Just G, Dahl K (1968) Tetrahedron 24:5251; b) Grundmann C, Richter R (1968) J Org Chem 33:476; c) Kim JN, Ryu EK (1990) Synth Commun 20:1373; d) Rai KML, Linganna N, Hassner A (1992) Org Prep Proc Int 24:91
Hassner A, Rai KML (1990) Heterocycles 30:817
Hassner A, Rai KML, Dehaen W (1994) Synth Commun 24:1669
Falb E, Nudelman A, Gottlieb HE, Hassner A (2000) Eur J Org Chem 645
Mukhopadhyay R, Datta S, Chattopadhyay P, Bhattacharjya A, Patra A (1996) Ind J Chem 35B:1190
For two earlier and lengthier syntheses, see: a) Snider BB, Faith WC (1984) J Am Chem Soc 106:1443; b) Rousch WR, Walts AE (1984) J Am Chem Soc 106:721; c) Walts AE, Rousch WR (1985) Tetrahedron 41:3623
Harbour GC, Tymiak AA, Rinehart KL Jr, Shaw PD, Hughes RG Jr, Mizak SA, Coats JH, Zurenko GE, Li LH, Kuentzel SL (1981) J Am Chem Soc 103:5604
a) Hassner A, Murthy KSK (1986) Tetrahedron Lett 27:1407; b) Murthy KSK, Hassner A (1991) Isr J Chem 31:239; c) Hassner A, Murthy KSK, Maurya R, Dehaen W, Friedman O (1994) J Heterocyclic Chem 31:687
Ihara M, Tokunaga Y, Taniguchi N, Fukumoto K (1991) Tetrahedron 47:6635
a) Masaki M, Fukui K, Ohta M (1967) J Org Chem 32:3564; b) Smith JH, Heidema JH, Kaiser ET (1972) J Am Chem Soc 94:9276; c) Hassner A, Alexanian V (1979) J Org Chem 44:3861; d) Oppolzer W, Battig K, Hudlicky T (1981) Tetrahedron 37:4359
a) Corey EJ, Melvin LS, Haslaugh MF (1975) Tetrahedron Lett 3117; b) Gilchrist TL (1983) Chem Soc Rev 12:53; c) Denmark SE, Dappen MS (1984) J Org Chem 49:798
a) Stevens CL, Gillis BT (1957) J Am Chem Soc 79:3448; for formation of a-bromoaldehydes via silylenol ethers see: Reuss RH, Hassner A (1974) J Org Chem 39:1785
Hassner A, Murthy KSK (1987) Tetrahedron Lett 28:683
a) Padwa A, Chiacchio U, Dean DC, Schoffstall AM, Hassner A, Murthy KSK (1988) Tetrahedron Lett 29:4169; b) Hassner A, Murthy KSK, Padwa A, Chiacchio U, Dean DC, Schoffstall AM (1989) J Org Chem 54:5277
For other examples of dipoles adding across a p-bond of a furan see: Heinze I, Eberbach W (1988) Tetrahedron Lett 2051
a) Hassner A, Murthy KSK (1987) Tetrahedron Lett 28:4097; b) Hassner A, Murthy KSK, Padwa A, Bullock WH, Stull PD (1988) J Org Chem 53:5063
Yao C-F, Yang C-S, Fang H-Y (1997) Tetrahedron Lett 38:6419
a) Yao C-F, Kao K-H, Liu J-T, Chu C-M, Wang Y, Chen W-C, Lin Y-M, Lin W-W, Yan M-C, Liu J-Y, Chuang M-C, Shiue J-L (1998) Tetrahedron 54:791; b) see also: Liu J-T, Lin W-W Jang J-J, Liu J-Y, Yan M-C, Huang C, Kao K-H, Wang Y, Yao C-F (1999) Tetrahedron 55:7115; Yan M-C, Liu J-Y, Lin W-W, Kao K-H, Liu J-T, Jang J-J, Yao C-F (1999) Tetrahedron 55:12,493 for the use of alkyl chloroformate for the generation of nitrile oxides and in the intramolecular alkoxycarbonyl nitronate-olefin cycloaddition
Murthy KSK, Hassner A (1987) Tetrahedron Lett 28:97
Hassner A, Amarasekara AS, Padwa A, Bullock WH (1988) Tetrahedron Lett 29:715
Yip C, Handerson H, Jordan R, Tam W (1999) Org Lett 1:791
a) Dogbéavou R, Breau L (1997) Synlett 1208; b) Marrugo H, Dogbéavou R, Breau L (1999) Tetrahedron Lett 40:8979
Hassner A, Dehaen W (1991) Chem Ber 124:1181
Enders D, Haertwig A, Runsink J (1998) Eur J Org Chem 1793
Dehaen W, Hassner A (1991) J Org Chem 56:896
Hirai Y, Nagaoka H (1997) Tetrahedron Lett 38:1969
Fernández-Mateos A, Coca GP, González RR, Hernández CT (1996) J Org Chem 61: 9097
Dehaen W, Hassner A (1990) Tetrahedron Lett 31:743
a) Gottlieb L, Hassner A (1995) J Org Chem 60:3759; b) Hassner A, Friedman O, Dehaen W (1997) Liebigs Ann 587; c) Namboothiri INN, Hassner A, Gottlieb HE (1997) J Org Chem 62:485
Garro-Helion F, Merzouk A, Guibe F (1993) J Org Chem 58:6109
Namboothiri INN, Hassner A (1996) J Organomet Chem 518:69
Armstrong P, Grigg R, Heaney F, Surendrakumar S, Warnock WJ (1991) Tetrahedron 47:4495
a) Lebel NA, Post ME, Whang JJ (1964) JACS 86:3759; b) We thank Prof. J. Leighton of Columbia University for this suggestion
a) Huisgen R, Grashey R, Hauck H, Seidl H (1968) Chem Ber 101:2043; b) Huisgen R (1976) J Org Chem 41:403; c) Leroy G, Nguyen MT, Sana M (1978) Tetrahedron 34:2459
a) Tufariello JJ, Ali SkA (1978) Tetrahedron Lett 19:4647; b) Tufariello JJ, Puglis JM (1986) Tetrahedron Lett 27:1265; c) Burdisso M, Gandolfi R, Grunanger P, Rastelli A (1990) J Org Chem 55:3427; d) Jung ME, Gervay J (1990) Chemtracts 3:284
a) Lebel NA, Banucci EG (1971) J Org Chem 36:2440; b) Burdisso M, Gandolfi R, Grunanger P (1989) Tetrahedron 45:5579
a) Bianchi G, Micheli CD, Gandolfi R (1979) Angew Chem Int Ed Engl 18:721; b) Bianchi G, Gandolfi R (1984) In: Padwa A (ed) 1,3-Dipolar cycloaddition chemistry. Wiley, New York, vol 2, chap 14
Huang KS-L, Lee EH, Olmstead MM, Kurth MJ (2000) J Org Chem 65:499
a) Cheng Q, Oritani T, Hassner A (2000) Synth Commun 30:293; b) Cheng Q, Hassner A (2000) (unpublished results)
Young DGJ, Gomez-Bengoa E, Hoveyda AH (1999) J Org Chem 64:692
Stepanov AV, Veselovsky VV (1997) Russ Chem Bull 46:1606
Stepanov AV, Lozanova AV, Veselovsky VV (1998) Russ Chem Bull 47:2286
a) Armstrong P, Grigg R, Warnock WJ (1987) J Chem Soc Chem Commun 1325; Grigg R (1987) J Chem Soc Rev 16:89; b) Padwa A, Norman BH (1988) Tetrahedron Lett 29:2417
Hassner A, Maurya R, Mesko E (1988) Tetrahedron Lett 29:5313
Oppolzer W, Keller K (1970) Tetrahedron Lett 1117
Hassner A, Maurya R, Friedman O, Gottlieb HE, Padwa A, Austin D (1993) J Org Chem 58:4539
Raban M, Kost D (1984) Tetrahedron 40:3345
Hassner A, Maurya R (1989) Tetrahedron Lett 30:5803
a) See Bennett JN (1980) Chem Rev 80:63 [7] for a recent review; b) Hassner A, Maurya R (1989) Tetrahedron Lett 30:2289; c) Hassner A, Maurya R, Padwa A, Bullock WH (1991) J Org Chem 56:2775
Gotoh M, Sun B, Hirayama K, Noguchi M (1996) Tetrahedron 52:887
Sun B, Adachi K, Noguchi M (1996) Tetrahedron 52:901
Mihailovic M, Rajkovic MM, Lorenc LB, Pavlovic VD, Milovanovic AZ, Tinant, B, Declercq J-P (1996) Tetrahedron 52:11995
a) Hassner A, Falb E, Nudelman A, Albeck A, Gottlieb HE (1994) Tetrahedron Lett 35:2397; b) Falb E, Bechor Y, Nudelman A, Hassner A, Albeck A, Gottlieb HE (1999) J Org Chem 64:498
Chiacchio U, Corsaro A, Pistara V, Rescifina A, Romeo G, Romeo R (1996) Tetrahedron 52:7875
a) Ishizuka T, Kunieda T (1987) Tetrahedron Lett 28:4185; b) Abd Elall EHM, Al Ashmawy MI, Mellor JM (1987) J Chem Soc Perkin Trans 1 2729
Hassner A, Murthy K (1987) Tetrahedron Lett 28:97
Hassner A, Stern M (1986) Angew Chem Int Ed Engl 25:478
For a review of triazoline decomposition by thermolysis and photolysis see: Scheiner P (1970) In: Thyagarajan (ed) Selective organic transformations. Wiley, vol 1, pp 327–362
Rai KML, Hassner A (1990) Heterocycles 30:817
Hassner A, Fibiger R, Amarasekara AS (1988) J Org Chem 53:22
Hassner A, Amarasekara AS, Andisik D (1988) J Org Chem 53:27
Schkeryantz JM, Pearson WH (1996) Tetrahedron 52:3107
Norris P, Horton D, Giridhar DE (1996) Tetrahedron Lett 37:3925
Krülle TM, de la Fuente C, Pickering L, Aplin RT, Tsitsanou KE, Zographos SE, Oikonomakos NG, Nash RJ, Griffiths RC, Fleet GW (1997) Tetrahedron: Asymmetry 8:3807
Molander GA, Hiersemann M (1997) Tetrahedron Lett 38:4347
Rai KML, Hassner A (1989) Synth Commun 19:2799
Gladstone WAF, Aylward JB, Norman ROC (1969) JCS Chem Commun 2587
a) Huisgen R, Seidel M, Sauer J, Mcfarland JW, Wallbillich G (1959) J Org Chem 24:892; b) Huisgen R, Sauer J, Seidel M (1961) Chem Ber 94:2503
Reimlinger H, Vandewalle JJM, King GSD, Lingier WRF, Merenyi R (1970) Chem Ber 103:1918
a) Sauer J, Mayer KK (1968) Tetrahedron Lett 325; b) Marky M, Meier H, Wunderli A, Hemigartner H, Schmid H, Hansen HJ (1978) Helv Chim Acta 61:1477
a) Ollis, WD, Ramseden CA (1976) Adv Heterocycl Chem 19:1; b) Gotthardt H, Reiter F (1979) Chem Ber 112:1206, 1635; c) Pfoertner KH, Foricher J (1980) Helv Chim Acta 63:653
Shawali AS, Hasseneen HM, Sherif SM (1980) J Heterocycl Chem 17:1745
a) Huisgen R, Seidel M, Wallbillich G, Knupfer H (1962) Tetrahedron 17:3; b) Hasseneen HM, Mousa HAM, Abed NM, Shawali AS (1988) Heterocycles 27:695; c) Hasseneen HM, Ead HA, Elwan NM, Shawali AS (1988) Heterocycles 27:2857; d) El-Abadellah MM, Hussein AQ, Kamal MR, Al-Adhami KH (1988) Heterocycles 27:917; e) Hegarty AF, Cashman MP, Scott FL (1972) JCS Perkin Trans 2 44; f) Baruah AK, Prajapathi D, Sandhu JS (1988) Tetrahedron 44:6137
Tezuka T, Otsuka T (1988) Chem Lett 1751
Gladstone WAF, Aylward JB, Norman ROC (1969) J Chem Soc 2587
Sicard G, Baceiredo A, Bertrand G (1988) J Am Chem Soc 110:2663
Liu B, Wang M-X, Huang Z-T (1999) Tetrahedron Lett 40:7399
Meier vH, Heimgartner H (1985) Helv Chim Acta 68:1283
Meier vH, Heimgartner H (1986) Helv Chim Acta 69:927
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2001 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Namboothiri, I.N.N., Hassner, A. (2001). Stereoselective Intramolecular 1,3-Dipolar Cycloadditions. In: Metz, P. (eds) Stereoselective Heterocyclic Synthesis III. Topics in Current Chemistry, vol 216. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-44726-1_1
Download citation
DOI: https://doi.org/10.1007/3-540-44726-1_1
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-41763-7
Online ISBN: 978-3-540-44726-9
eBook Packages: Springer Book Archive