Synthesis and anionically induced domino reactions of chiral α-bromo α,β-unsaturated esters

被引：0

作者：

Braun, NA ^{[1
]}

Burkle, U ^{[1
]}

Feth, MP ^{[1
]}

Klein, I ^{[1
]}

Spitzner, D ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 1998卷 / 08期

关键词：

asymmetric dihydroxylation (Sharpless-AD); Wittig olefination; alpha-bromo alpha; beta-unsaturated esters; diastereoselective aprotic Michael domino reaction; tricyclo[3.2.1.0(2,7)] octanes;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral alpha-bromo alpha,beta-unsaturated esters 3 and 9 are prepared by asymmetric Sharpless dihydroxylation (AD) of 5 and from ester 7 and the chiral diols 8 by transacetalization, respectively. Both types of alpha-bromo alpha,beta-unsaturated ester react with the kinetic Lithium dienolates of enone 10 to give functionalized tricyclo[3.2.1.0(2,7)]octanes 11. Esters 3 give one single diastereomer (de greater than or equal to 95%), whereas mixtures of diastereomers (de 28 to 46%) are obtained with the esters 9.

引用

页码：1569 / 1576

页数：8

共 50 条

[21] Domino reactions in organic synthesis
Chemistry and Industry (London), 1995, (12):
[22] Domino reactions in organic synthesis
Tietze, LF
CHEMICAL REVIEWS, 1996, 96 (01) : 115 - 136
[23] Development of Domino Reactions with β-Enamino Esters as Key Intermediates
Han, Ying
Sun, Ling
Sun, Yan
Gao, Hong
Yan, Chaoguo
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (09) : 1577 - 1586
[24] An Efficient Asymmetric Domino Reaction of Amino Aldehyde to β,γ-Unsaturated α-Keto Esters Using trans-Perhydroindolic Acid as a Chiral Organocatalyst
Shen Jiefeng
An Qianjin
Liu Delong
Liu Yangang
Zhang Wanbin
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (11) : 2681 - 2687
[25] A facile synthesis of α-phenylchalcogeno(S, Se) α,β-unsaturated esters from ethyl α-bromo-α-phenylchalcogeno acetates
Silveira, CC
Botega, CS
Rhoden, CRB
Nunes, MRS
Braga, AL
Lenardáo, EJ
SYNTHETIC COMMUNICATIONS, 1998, 28 (18) : 3371 - 3380
[26] Stereoselective Synthesis of (2Z)-a-Bromo-a, QQ -Unsaturated Esters Via Arsonium Ylide
Synth Commun, 4 (677):
[27] Domino reactions of diazodicarbonyl compounds with α,β-unsaturated δ-amino esters: a convenient way towards 2-oxopiperidines, dihydropyridinones and isoquinolinediones
Medvedev, J. J.
Meleshina, M. V.
Panikorovskii, T. L.
Schneider, C.
Nikolaev, V. A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (34) : 9107 - 9117
[28] REACTION OF ALPHA-BROMO-ALPHA,BETA-UNSATURATED ESTERS AND BUTENOLIDES WITH MALONAMIC ESTERS
TAKEI, H
FUKUDA, Y
SUGAYA, K
TAGUCHI, T
KAWARA, T
CHEMISTRY LETTERS, 1980, (10) : 1307 - 1310
[29] Highly enantioselective epoxidation of α,β-unsaturated esters by chiral dioxirane
Wu, XY
She, XG
Shi, YA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) : 8792 - 8793
[30] Preparation of chiral propargylic alcohols from α,β-unsaturated esters
Chun, J
Byun, HS
Bittman, R
TETRAHEDRON LETTERS, 2002, 43 (45) : 8043 - 8045

← 1 2 3 4 5 →