Investigations into the enantioselective protonation of enolates derived from 2-methyl-1-tetralone using a chiral diamine ligand

被引：19

作者：

Eames, J ^{[1
]}

Weerasooriya, N ^{[1
]}

机构：

[1] Univ London Queen Mary & Westfield Coll, Dept Chem, London E1 4NS, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(99)02109-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of enantiomerically enriched (+)-(R)-2-methyl-1-tetralone 1 (up to 47% e.e.) was achieved by enantioselective protonation of an achiral lithium enolate 3 using a chiral diamine additive in the presence of acetic acid. We discuss the factors (like salt effects and chelation) that are responsible for this observed enantioselectivity and comment on the role of the achiral acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：521 / 523

页数：3

共 7 条

[1] Efficient asymmetric protonation of enolates with readily accessible chiral α-sulfinyl alcohols [J].

Asensio, G ;

Alemán, P ;

Cuenca, A ;

Gil, J ;

Medio-Simón, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :4073-4078

[2] Diastereoselective protonation of chiral enolates derived from 2,4-dimethyl-1-tetralone using carbonyl chelating proton donors [J].

Eames, J .

TETRAHEDRON LETTERS, 1999, 40 (31) :5787-5790

[3] PROTON TRANSFER ACID-BASE CATALYSIS + ENZYMATIC HYDROLYSIS .I. ELEMENTARY PROCESSES [J].

EIGEN, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (01) :1-&

[4]

Fehr C., 1996, Angew. Chem., V35, P2566

[5] Asymmetric protonation of enolic species: Dramatic increase in the selectivity with temperature and unexpected Eyring diagram [J].

Muzart, J ;

Henin, F ;

Aboulhoda, SJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (03) :381-389

[6] ASYMMETRIC PROTONATION OF ENOLATES [J].

POTIN, D ;

WILLIAMS, K ;

REBEK, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1420-1422

[7] ENANTIOSELECTIVE PROTONATION OF ACHIRAL LITHIUM ENOLATES USING A CHIRAL AMINE IN THE PRESENCE OF LITHIUM BROMIDE [J].

YASUKATA, T ;

KOGA, K .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :35-38

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