Abstract
Chemists have available nowadays a rich palette of known synthetic processes. These may be used in synthetic planning and can be incorporated in suitable synthetic strategies. An important example involves the controlled generation of compounds containing more sp3 carbons from precursors mainly containing sp2 carbons. Absolute asymmetric synthesis by using circularly polarized light remains of limited application, but convenient methods have been introduced for asymmetric (photochemical) synthesis. The interaction with organocatalysis has open new perspectives.
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References
Schwartz BD, Matoušovà E, White R, Banwell MG, Willis AC (2013) A chemoenzymatic total synthesis of the protoilludane aryl ester (+)-Armillarivin. Org Lett 15:1934–1937
Chen IT, Baitinger I, Schreyer L, Trauner D (2014) Total synthesis of sandresolide B and amphilectolide. Org Lett 16:166–169
Zhang FM, Peng L, Li H, Ma AJ, Peng JB, Guo JJ, Yang D, Hou SH, Tu YQ, Kitching W (2012) Total synthesis of the nominal didemnaketal A. Angew Chem Int Ed 51:10846–10850
Winter DK, Endoma-Arias MA, Hudlicky T, Beutler JA, Porco JA Jr (2013) Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue. J Org Chem 78:7617–7626
Araneda JF, Neue Bm Piers WE, Parvez M (2012) Photochemical synthesis of a ladder diborole: a new boron-conjugate material. Angew Chem Int Ed 51:8546–8550
Gritsch PJ, Leitner C, Pfaffenbach M, Gaick T (2014) The Witkop cyclization a photochemical indole CH activation. Angew Chem Int Ed 53:1208–1217
Toelle N, Weinstabl H, Gaich T, Mulzer J (2014) Light-mediated total synthesis of 17-deoxyprovidencin. Angew Chem Int Ed 53:3859–3862
Xu J, Caro-Diaz EJE, Lakoske MH, Hung CI, Jamora C, Theodorakis EA (2012) Nature-inspired synthesis of (-)-fusarisetin A. J Am Chem Soc 134:5072–5075
Kumar NNB, Mukhina OA, Kutateladze AG (2013) Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores. J Am Chem Soc 135:9608–9611
Wender PA, Siggel L, Nuss JM (1989) Arene-alkene photocycloaddition reactions. Org Photochem 10:357–473
Maskill KG, Knowles JP, Elliott LD, Alder RW, Booker-Milburn KI (2013) Complexity from simplicity: tricyclic aziridines from the rearrangement of pyrroles by batch and flow photochemistry. Angew Chem Int Ed 52:1499–1500
Natarajan A, Ng D, Yang Z, Garcia-Garibay MA (2007) Parallel syntheses of (+)- and (-)-α-cuparenone by radical combination in the crystalline solids. Angew Chem Int Ed 46:6485–6487
Hoffan N (2014) Photochemical reactions applied to the synthesis of helicenes and helicene-like compounds. J Photochem C Phochem Rev 19:1–10
Gingras M, Fèlix G, Peresutti R (2013) One hundred years of helicene chemistry. Part 2: Stereoselective syntheses and chiral separations of carbohelicenes. Chem Soc Rev 32:1007–1050
Meinert C, Hoffmann SV, Cassam-Chena P, Evans AC, Giri C, Nahon L, Maierhenrich UJ (2014) Photoenergy-controlled symmetry breaking with circularly polarized light. Angew Chem Int Ed 53:210–214
Bredehöft JH, Jones NC, Meinert C, Evans AC, Hoffmann SV, Meierhenrich UJ (2014) Understanding photochirogenesis: Solvent effects on circular dichroism and anisotropy spectroscopy. Chirality 26:373–378
Inoue Y (1992) Asymmetric photochemical reactions in solutions. Chem Rev 92:741–770
Hoffmann N (2014) Photochemical reactions applied to the synthesis of helicenes and helicene-like compounds. J Photochem Photobiol C Photochem Rev 19:1–19
Mori T, Inoue Y (2013) Charge-transfer excitation: unconventional yet practical means for controlling stereoselectivity in asymmetric photoreactions. Chem Soc Rev 42:8122–8133
Wessig P (2006) Organocatalytic enantioselective photoreactions. Angew Chem Int Ed 45:2168–2171
Müller C, Bach T (2008) Chiral control in photochemical reactions: enantioselective formation of complex photoproduct in solution. Aust J Chem 62:557–564
Yang C, Inoue Y (2014) Supramolecular photochirogenics. Chem Soc Rev 43:4123–4243
Nijland A, Harutyunyan SR (2013) Light on the horizon? Catalytic enantioselective photoreactions. Catal Sci Tech 3:1180–1189
Brimioulle R, Bach T (2013) Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions. Science 342:840–843
Arceo E, Jurberg ID, Alvarez-Fernandez A, Melchiorre P (2013) Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes. Nat Chem 5:750–755
Arceo E, Bahamonde A, Bergonzini G, Melchiorre P (2014) Enantioselective direct α-alkylation of cyclic ketones by means of photoorganocatalysis. Chem Sci 5:2438–2442
Cecere G, König CM, Alleva JL, MacMillan DWC (2013) Enantioselective direct α-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling. J Am Chem Soc 135:11521–11524
Kumarasamy E, Ragunathan R, Jockush S, Ugrinov A, Sivaguru J (2014) Tailoring atropisomeric maleimides for stereospecific [2+2] photocycloaddition. Photochemical and photophysical investigations leading to visible light photocatalysis. J Am Chem Soc 136:8729–8737
Kumarasamy E, Sivaguru J (2013) Light-induced stereospecific intramolecular [2+2]-cycloaddition of atropisomeric 3,4-dihydro-2-pyridones. Chem Commun 49:4346–4348
Kumarasamy E, Omlid JN, Ugrinov A, Sivaguru J (2011) Light-induced enantiospecific 4π ring closure of axially chiral 2-pyridones: enthalpic and entropic effects promoted by H-bonding. J Am Chem Soc 133:17106–17109
Jesuraj JL, Sivaguru J (2010) Photochemical type II reaction of atropchiral benzoylformamides to point chiral oxazolidin-4-ones. Axial chiral memory leading to enantiomeric resolution of photoproducts. Chem Commun 46:4791–4793
Raghunathan R, Kumarasamy E, Iyer A, Ugrinov A, Sivaguru J (2013) Intramolecular Paternò-Büchi reaction of atropisomeric α-oxoamides in solution and in the solid-state. Chem Commun 49:8713–8715
Vallavoju N, Selvakumar S, Jockush S, Sibi MP, Sivaguru J (2014) Enantioselective organo-photocatalysis mediated by atropisomeric thiourea derivatives. Angew Chem Int Ed 53:5604–5608
Du J, Skubi KL, Schultz DM, Yoon TP (2014) A dual-catalysis approach to enantioselective [2+2] photocycloadditions using visible light. Science 344:392–396
Lian M, Li Z, Cai Y, Meng Q, Gao Z (2012) Enantioselective photooxygenation of β-keto esters by chiral phase transfer catalysis using molecular oxygen. Chem Asian J 7:2019–2023
Ke C, Yang C, Mori T, Wada T, Liu Y, Inoue Y (2009) Catalytic enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by a non-sensitizing chiral metallosupramolecular host. Angew Chem Int Ed 48:6675–6677
Fuentealba D, Kato H, Nishijima M, Fukuhara G, Mori T, Inoue Y, Bohne C (2013) Explaining the high enantiomeric photocyclodimerization of 2-anthracenecarboxylate bound to human serum albumin using time-resolved anisotropy studies. J Am Chem Soc 135:203–209
Pengyan W, Cheng H, Jian W, Xiaojun P, Xuezhao L, Yonglin A, Chunying D (2012) Photoactive chiral metal-organic frameworks for light-driven asymmetric α-alkylation of aldehydes. J Am Chem Soc 134:14991–14999
Alonso R, Bach T (2014) A chiral thioxanthone as an organocatalyst for enantioselective [2+2] photocycloaddition reactions induced by visible light. Angew Chem Int Ed 53:4368–4371
Maturi MM, Bach T (2014) Enantioselective catalysis of the intermolecular [2+2] photocycloaddition between 2-pyridones and acetylenedicarboxylates. Angew Chem Int Ed 53:7661–7664
Liao HH, Hsiao CC, Sugiono E, Rueping M (2013) Shedding light on Brønsted acid catalysis a photocyclization-reduction reaction for the asymmetric synthesis of tetrahydroquinolines from aminocalchones in batch and in flow. Chem Commun 49:7953–7955
Rono LJ, Yayla HG, Wang DY, Armstrong MF, Knowles RR (2013) Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: development of an asymmetric aza-pinacol cyclization. J Am Chem Soc 135:17735–17738
Wang J, Feringa BL (2011) Dynamic control of chiral space in a catalytic asymmetric reaction using a molecular motor. Science 331:1429–1432
Šumanovac-Ramljak T, Sohora M, Antol I, Kontrec D, Basarić N, Mlinarić-Majerski K (2014) Memory of chirality in the phthalimide photocyclization of adamantane dipeptides. Tetrahedron Lett 55:4078–4081
Griesbeck AG, Kramer W, Lex J (2001) Diastereo- and enantioselective synthesis if pyrrolo[1,4]benzodiazepines through decarboxylative photocyclization. Angew Chem Int Ed 40:577–579
Hong BC, Lin CW, Liao WK, Lee GH (2013) Sequential asymmetric catalysis in Michael-Michael-Michael aldol reactions: merging organocatalysis with photoredox catalysis in a one-pot enantioselective synthesis of highly functionalized decalines bearing a quaternary carbon stereocenter. Org Lett 15:6258–6261
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Albini, A. (2016). Photochemical and Photocatalyzed Synthesis. In: Photochemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-47977-3_8
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DOI: https://doi.org/10.1007/978-3-662-47977-3_8
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-47976-6
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