Enantioselective Lewis Acid Catalysis in Intramolecular [2+2] Photocycloaddition Reactions of Coumarins

被引：118

作者：

Guo, Hao ^{[1
,2
]}

Herdtweck, Eberhardt ^{[1
,2
]}

Bach, Thorsten ^{[1
,2
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

[2] Tech Univ Munich, CRC, D-85747 Garching, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 42期

关键词：

chirality; cycloadditions; enantioselectivity; Lewis acids; photochemistry; SUPERCRITICAL CARBON-DIOXIDE; PHOTOCHEMICAL-REACTIONS; ASYMMETRIC PHOTOCHEMISTRY; PHOTODIMERIZATION; STEREOCHEMISTRY; PHOTOADDITION; CYCLOADDITION; CHIRALITY; ALCOHOLS; ALKENES;

D O I：

10.1002/anie.201003619

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Photochemistry goes acidic! In the presence of the chiral Lewis acid catalyst 2 the intramolecular [2+2] photocycloaddition of 4-(alk-4- enyl)coumarins (1) provides the corresponding products 3 with up to four stereogenic centers in a highly chemo-(84-89 % yield) and stereoselective fashion. For R=H, enantioselectivities up to 82 % ee are possible with 50 mol % catalyst 2 and up to 78 % ee with only 20 mol % of catalyst 2. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7782 / 7785

页数：4

共 57 条

[31]

Margaretha P, 2005, MOL SUPRAM PHOTOCHEM, V12, P211

[32]

Mattay J., 1995, METHODEN ORG CHEM C, P3085

[33] SOLVENT EFFECTS ON PHOTODIMERIZATION OF COUMARIN [J].

MORRISON, H ;

CURTIS, H ;

MCDOWELL, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (23) :5415-&

[34] Chirality control in photochemical reactions:: Enantioselective formation of complex photoproducts in solution [J].

Mueller, Christiane ;

Bach, Thorsten .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (08) :557-564

[35] Light-Driven Enantioselective Organocatalysis [J].

Mueller, Christiane ;

Bauer, Andreas ;

Bach, Thorsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6640-6642

[36]

Muller C., 2009, ANGEW CHEM, V121, P6767

[37] Enantiodifferentiating photoaddition of alcohols to 1,1-diphenylpropene in supercritical carbon dioxide: Sudden jump of optical yield at the critical density [J].

Nishiyama, Y ;

Kaneda, M ;

Saito, R ;

Mori, T ;

Wada, T ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6568-6569

[38] Entrainer effect on photochirogenesis in near- and supercritical carbon dioxide: Dramatic enhancement of enantioselectivity [J].

Nishiyama, Yasuhiro ;

Wada, Takehiko ;

Asaoka, Sadayuki ;

Mori, Tadashi ;

McCarty, Taylor A. ;

Kraut, Nadine D. ;

Bright, Frank V. ;

Inoue, Yoshihisa .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) :7526-+

[39] Mechanistic study on the enantiodifferentiating anti-Markovnikov photoaddition of alcohols to 1,1-diphenyl-1-alkenes in near-critical and supercritical carbon dioxide [J].

Nishiyama, Yasuhiro ;

Kaneda, Masayuki ;

Asaoka, Sadayuki ;

Saito, Ryota ;

Mori, Tadashi ;

Wada, Takehiko ;

Inoue, Yoshihisa .

JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (51) :13432-13440

[40]

Pons J.-M., 1995, Lewis Acids and Selectivity in Organic Synthesis

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