Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes

被引：16

作者：

Florio, S

Capriati, V

Luisi, R

Abbotto, A

机构：

[1] Univ Bari, Dipartimento Farmacochim, CNR, Ctr Studio Metodol Innovat Sintesi Organ, I-70125 Bari, Italy

[2] Univ Milan, Dipartimento Sci Mat, I-20125 Milan, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 41期

关键词：

boron azaenolates; chiral oxazolines; chiral chlorohydrins; oxiranyl oxazolines; formyl epoxides;

D O I：

10.1016/S0040-4039(99)01480-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7421 / 7425

页数：5

相关论文

共 14 条

[1] METAL-ASSISTED ALDOL CONDENSATION OF CHIRAL ALPHA-HALOGENATED IMIDE ENOLATES - A STEREOCONTROLLED CHIRAL EPOXIDE SYNTHESIS [J].

ABDELMAGID, A ;

PRIDGEN, LN ;

EGGLESTON, DS ;

LANTOS, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4595-4602

[2] THE RATIONAL DESIGN AND SYSTEMATIC ANALYSIS OF ASYMMETRIC ALDOL REACTIONS USING ENOL BORINATES - APPLICATIONS OF TRANSITION-STATE COMPUTER MODELING [J].

BERNARDI, A ;

GENNARI, C ;

GOODMAN, JM ;

PATERSON, I .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2613-2636

[3] PREPARATION OF FUNCTIONALIZED OXAZOLINES [J].

BRETON, P ;

ANDREBARRES, C ;

LANGLOIS, Y .

SYNTHETIC COMMUNICATIONS, 1992, 22 (17) :2543-2554

[4] ASYMMETRIC-SYNTHESIS OF ANTI-BETA-HYDROXY-ALPHA-AMINO ACIDS [J].

EVANS, DA ;

SJOGREN, EB ;

WEBER, AE ;

CONN, RE .

TETRAHEDRON LETTERS, 1987, 28 (01) :39-42

[5] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[6] An oxazoline-mediated synthesis of formyl epoxides [J].

Florio, S ;

Capriati, V ;

Luisi, R .

TETRAHEDRON LETTERS, 1996, 37 (27) :4781-4784

[7]

FLORIO S, UNPUB EUR J ORG CHEM

[8] ENOLBORATION .5. AN EXAMINATION OF THE EFFECTS OF AMINE, SOLVENT, AND OTHER REACTION PARAMETERS ON THE STEREOSELECTIVE ENOLBORATION OF KETONES WITH VARIOUS CHX(2)BX REAGENTS - AN OPTIMIZED PROCEDURE TO ACHIEVE THE STEREOSELECTIVE SYNTHESIS OF E-ENOL BORINATES FROM REPRESENTATIVE KETONES USING CHX(2)BCL/ET(3)N [J].

GANESAN, K ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7162-7169

[9] Synthesis of optically active 2-chloromethyl-2-oxazolines by the ortho-ester condensation method using triethyl orthochloroacetate [J].

Kamata, K ;

Sato, H ;

Takagi, E ;

Agata, I ;

Meyers, AI .

HETEROCYCLES, 1999, 51 (02) :373-378

[10]

MASAMUNE S, 1979, TETRAHEDRON LETT, V19, P1665