Abstract
The stereoisogram approach concludes that chirality and RS-stereogenicity are independent concepts and that prochirality and pro-RS-stereogenicity are independent concepts. Accordingly, the conventional approach should be reorganized, where such confused terms as “chirality”, “stereogenicity”, “prochirality”, and “prostereogenicity” should be replaced by newly-defined attributive terms based on the stereoisogram approach, e.g., chirality (as a purely geometric term), RS-stereogenicity, prochirality (as a purely geometric term), and pro-RS-stereogenicity. Such relational terms as “enantiotopic”, “diastereotopic”, and “stereoheterotopic” in the conventional approach should be replaced by newly-defined relational terms based on the stereoisogram approach, e.g., enantiotopic (as a purely geometric term), RS-diastereotopic, and RS-stereoheterotopic.
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References
Black KA (1990) J Chem Educ 67:141–142
Cahn RS, Ingold CK, Prelog V (1966) Angew Chem Int Ed Engl 5:385– 415
Eliel EL (1982) Top Curr Chem 105:1–76
Eliel EL, Wilen SH (1994) Stereochemistry of organic compounds. Wiley, New York
Eliel EL, Willen SH, Doyle MP (2001) Basic organic stereochemistry. Wiley-Interscience, New York
Fujita S (1990) J Am Chem Soc 112:3390–3397
Fujita S (1991a) Tetrahedron 47:31–46
Fujita S (1991b) Symmetry and Combinatorial enumeration in chemistry. Springer, Berlin/Heidelberg
Fujita S (2000a) J Chem Inf Comput Sci 40:426–437
Fujita S (2000b) Tetrahedron 56:735–740
Fujita S (2001) Bull Chem Soc Jpn 74:1585–1603
Fujita S (2002a) J Org Chem 67:6055–6063
Fujita S (2002b) Bull Chem Soc Jpn 75:1863–1883
Fujita S (2002c) Chem Rec 2:164–176
Fujita S (2004a) J Math Chem 35:265–287
Fujita S (2004b) MATCH Commun Math Comput Chem 52:3–18
Fujita S (2004c) Tetrahedron 60:11629–11638
Fujita S (2004d) J Org Chem 69:3158–3165
Fujita S (2005a) Theor Chem Acc 113:73–79
Fujita S (2005b) Theor Chem Acc 113:80–86
Fujita S (2005c) MATCH Commun Math Comput Chem 54:251–300
Fujita S (2005d) MATCH Commun Math Comput Chem 53:147–159
Fujita S (2005e) MATCH Commun Math Comput Chem 54:39–52
Fujita S (2006a) MATCH Commun Math Comput Chem 55:237–270
Fujita S (2006b) Tetrahedron 62:691–705
Fujita S (2006c) Theor Chem Acc 115:37–53
Fujita S (2006d) MATCH Commun Math Comput Chem 55:5–38
Fujita S (2007a) MATCH Commun Math Comput Chem 57:299–340
Fujita S (2007b) MATCH Commun Math Comput Chem 58:611–634
Fujita S (2007c) Diagrammatical approach to molecular symmetry and enumeration of stereoisomers. University of Kragujevac, Faculty of Science, Kragujevac
Fujita S (2007d) MATCH Commun Math Comput Chem 57:265–298
Fujita S (2007e) J Comput Chem Jpn 6:73–90
Fujita S (2007f) Theor Chem Acc 117:353–370
Fujita S (2007g) Theor Chem Acc 117:339–351
Fujita S (2007h) J Math. Chem 42:481–534
Fujita S (2007i) MATCH Commun Math Comput Chem 57:5–48
Fujita S (2007j) J Comput Chem Jpn 6:59–72
Fujita S (2007k) MATCH Commun Math Comput Chem 58:5–45
Fujita S (2008a) J Math Chem 43:141–201
Fujita S (2008b) Yuki Gosei Kagaku Kyokai-Shi/J Synth Org Chem Jpn 66:995–1004
Fujita S (2009a) MATCH Commun Math Comput Chem 61:71–115
Fujita S (2009b) Tetrahedron 65:1581–1592
Fujita S (2009c) J Comput Aided Chem 10:76–95
Fujita S (2009d) J Comput Aided Chem 10:16–29
Fujita S (2009e) MATCH Commun Math Comput Chem 61:11–38
Fujita S (2009f) MATCH Commun Math Comput Chem 61:39–70
Fujita S (2009g) MATCH Commun Math Comput Chem 62:65–104
Fujita S (2009h) MATCH Commun Math Comput Chem 62:23–64
Fujita S (2010a) MATCH Commun Math Comput Chem 63:3–24
Fujita S (2010b) J Math Chem 47:145–166
Fujita S (2010c) MATCH Commun Math Comput Chem 63:25–66
Fujita S (2010d) Bull Chem Soc Jpn 83:1–18
Hanson KR (1966) J Am Chem Soc 88:2731–2742
Helmchen G (1996) A. General aspects. 1. Nomenclature and vocabulary of organic stereochemistry. In: Helmchen G, Hoffmann RW, Mulzer J, Schaumann E (eds) Stereoselective Synthesis. Methods of Organic Chemistry (Houben-Weyl), Workbench Edition E21, vol 1, 4th edn. Georg Thieme, Stuttgart, New York, pp 1–74
Hirschmann H (1983) Trans N Y Acad Sci Ser II 41:61–69
Hirschmann H, Hanson KR (1971a) Eur J Biochem 22:301–309
Hirschmann H, Hanson KR (1971b) J Org Chem 36:3293–3306
IUPAC Chemical Nomenclature and Structure Representation Division (2004) Provisional Recommendations. Nomenclature of Organic Chemistry http://www.iupac.org/reports/provisional/abstract04/favre_310305.html. Accessed date June 17, 2011
IUPAC Organic Chemistry Division (1996) Pure Appl Chem 68:2193–2222
Jonas J (1988) Coll Czech Chem Commun 53:2676–2714
McCasland GE (1953) A New General System for the Naming of Stereoisomers. Chemical Astracts, Columbus
Mislow K (1965) Introduction to Stereochemistry. Benjamin, New York
Mislow K (1977) Bull Soc Chim Belg 86:595–601
Mislow K (2002) Chirality 14:126–134
Mislow K, Raban M (1967) Top Stereochem 1:1–38
Mislow K, Siegel J (1984) J Am Chem Soc 106:3319–3328
Morris DG (2001) Stereochemistry. Royal Soc Chem, Cambridge
North N (1998) Principles and Applications of Stereochemistry. Stanley Thornes, Cheltenham
Prelog V, Helmchen G (1972) Helv Chim Acta 55:2581–2598
Prelog V, Helmchen G (1982) Angew Chem Int Ed Eng 21:567–583
Vollhardt KPC, Schore NE (2003) Organic Chemistry. Structure and Function, 4th edn. Freeman, New York
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Fujita, S. (2011). Prochirality and Pro-RS-Stereogenicity. Stereoisogram Approach Free from the Conventional “Prochirality” and “Prostereogenicity”. In: Putz, M. (eds) Carbon Bonding and Structures. Carbon Materials: Chemistry and Physics, vol 5. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-1733-6_10
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