Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: simple, selective access to chiral bicyclic lactams

被引：21

作者：

Aydogan, F

Demir, AS ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

[2] Yildiz Tech Univ, Dept Chem, TR-34010 Istanbul, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 02期

关键词：

D O I：

10.1016/j.tetasy.2003.11.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amino alcohols and 5-chloro-3-pentene-2-one. The photooxygenation of these compounds in the presence of a photosynthesizer furnishes the pyrrolooxazolone structures in high diastereoselectivities. In all of the examples, trans-isomers are formed as the major products. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：259 / 265

页数：7

相关论文

共 39 条

[1] Enantiomeric impurities in chiral catalysts, auxiliaries, synthons and resolving agents. Part 2 [J].

Armstrong, DW ;

He, LF ;

Yu, T ;

Lee, JT ;

Liu, YS .

TETRAHEDRON-ASYMMETRY, 1999, 10 (01) :37-60

[2] BICYCLIC ENDOPEROXIDES AND SYNTHETIC APPLICATIONS [J].

BALCI, M .

CHEMICAL REVIEWS, 1981, 81 (01) :91-108

[3] Tritylallyldimethylsilane-TiCl4 annulations to electron deficient olefins. Diastereomerically pure 3-substituted and 3,4-disubstituted cyclopentanols [J].

Brengel, GP ;

Meyers, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3230-3231

[4] ASYMMETRIC DIELS-ALDER REACTIONS - A ROUTE TO CHIRAL CARBOCYCLES VIA BICYCLIC LACTAMS [J].

BUSACCA, CA ;

MEYERS, AI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10) :2299-2316

[5] The synthesis of chiral 5-methylene pyrrol-2(5H)-ones via photooxygenation of homochiral 2-methylpyrrole derivatives [J].

Demir, AS ;

Aydogan, F ;

Akhmedov, IM .

TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :601-605

[6] Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives [J].

Demir, AS ;

Akhmedov, IM ;

Sesenoglu, Ö ;

Alptürk, O ;

Apaydin, S ;

Gerçek, Z ;

Ibrahimzade, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (10) :1162-1167

[7]

DEMIR AS, 1997, TETRAHEDRON-ASYMMETR, V5, P7535

[8] THE PHOTOCHEMICAL-SYNTHESIS OF FINE CHEMICALS WITH SUNLIGHT [J].

ESSER, P ;

POHLMANN, B ;

SCHARF, HD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (20) :2009-2023

[9] Synthesis of chiral condensed S-heterocycles via stereoselective Michael-like addition to butenolides and alpha,beta-unsaturated lactams [J].

Faltz, H ;

Bohrisch, J ;

Wohlauf, W ;

Patzel, M ;

Jones, PG ;

Liebscher, J .

TETRAHEDRON, 1996, 52 (27) :9035-9046

[10] CHEMISTRY OF SINGLET OXYGEN .4. OXYGENATIONS WITH HYPOCHLORITE-HYDROGEN PEROXIDE [J].

FOOTE, CS ;

WEXLER, S ;

ANDO, W ;

HIGGINS, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (04) :975-&

← 1 2 3 4 →