An unusual enhancement of chiral induction by chiral 2-imidazolidinone auxiliaries

被引：22

作者：

Abdel-Aziz, AAM ^{[1
]}

Okuno, J ^{[1
]}

Tanaka, S ^{[1
]}

Ishizuka, T ^{[1
]}

Matsunaga, H ^{[1
]}

Kunieda, T ^{[1
]}

机构：

[1] Kumamoto Univ, Fac Pharmaceut Sci, Kumamoto 8620973, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(00)01547-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselectivity which is induced by the use of 2-imidazolidinone auxiliaries is greatly dependent on the N-substituents of the heterocycles, among which the bulky arenesulfonyl group is the moiety of choice. Reactions of this type afford an excellent level of diastereoselection in the methylation of N'-butyryl-2-imidazolidinones via the metal enolates. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：8533 / 8537

页数：5

共 13 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2]

[Anonymous], [No title captured]

[3] TRANSITION-STATE PI-SOLVATION BY AROMATIC RINGS - AN ELECTRONIC CONTRIBUTION TO DIELS-ALDER REACTION DIASTEREOSELECTIVITY [J].

EVANS, DA ;

CHAPMAN, KT ;

HUNG, DT ;

KAWAGUCHI, AT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1184-1186

[4] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739

[5] Catalytic process for efficient enantiodivergence of meso-N,N′-diacetyl-2-imidazolidinones and dl-N-acetyl-2-oxazolidinones [J].

Hashimoto, N ;

Ishizuka, T ;

Kunieda, T .

TETRAHEDRON LETTERS, 1998, 39 (35) :6317-6320

[6] PRACTICAL PREPARATION OF CHIRAL 4-SUBSTITUTED 2-OXAZOLIDINONES [J].

ISHIZUKA, T ;

KIMURA, K ;

ISHIBUCHI, S ;

KUNIEDA, T .

CHEMISTRY LETTERS, 1992, (06) :991-994

[7] Isocyanates.: Part 5.: Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP-catalyzed isocyanation of amines with di-tert-butyl dicarbonate [J].

Knölker, HJ ;

Braxmeier, T .

TETRAHEDRON LETTERS, 1998, 39 (51) :9407-9410

[8] CONFORMATIONALLY RIGID CHIRAL [4+2]CYCLOADDUCT-BASED 2-OXAZOLIDINONES AS NEW AUXILIARIES [J].

MATSUNAGA, H ;

KIMURA, K ;

ISHIZUKA, T ;

HARATAKE, M ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1991, 32 (52) :7715-7718

[9] Asymmetric exo-selective Diels-Alder reactions by steric attenuation of secondary orbital interactions [J].

Powers, TS ;

Jiang, WQ ;

Su, J ;

Wulff, WD ;

Waltermire, BE ;

Rheingold, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6438-6439

[10] Dibutylboron triflate promoted conjugate addition of benzylic and allylic organocopper reagents to chiral alpha,beta-unsaturated N-acyl imidazolidinones [J].

vanHeerden, PS ;

Bezuidenhoudt, BCB ;

Ferreira, D .

TETRAHEDRON LETTERS, 1997, 38 (10) :1821-1824

← 1 2 →