HIGHLY STEREOSELECTIVE SYNTHESES INVOLVING N-ALKYL-4,4,7-ALPHA-TRIMETHYL-TRANS-OCTAHYDRO-1,3-BENZOXAZINE INTERMEDIATES .2.

被引：83

作者：

ELIEL, EL

HE, XC

机构：

[1] W. R. Kenan, Jr. Laboratories, Department of Chemistry, University of North Carolina, North Carolina 27599-3290, Chapel Hill

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 07期

关键词：

D O I：

10.1021/jo00294a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previously studied highly stereoselective additions of Grignard, organolithium, and hydride reagents to the 2-benzoyl derivative of compound la have been extended to other 2-alkanoyl derivatives (1, R = methyl, ethyl, isopropyl) and to the 2-benzoyl derivative with R = methyl. High diastereoselectivity is attained in most of the products. © 1990, American Chemical Society. All rights reserved.

引用

页码：2114 / 2119

页数：6

共 18 条

[1] ORGANOSULFUR CHEMISTRY .3. NMR-SPECTRA OF CARBANIONS DERIVED FROM 1,3-DITHIANES AS RELATED TO HIGH STEREOSELECTIVITY IN THEIR REACTIONS WITH ELECTROPHILES [J].

ABATJOGLOU, AG ;

ELIEL, EL ;

KUYPER, LF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8262-8269

[2]

ADGER BM, 1987, SYNTHESIS-STUTTGART, P53

[3] SELECTIVE REDUCTIONS .29. A SIMPLE TECHNIQUE TO ACHIEVE AND ENHANCED RATE OF REDUCTION OF REPRESENTATIVE ORGANIC-COMPOUNDS BY BORANE-DIMETHYL SULFIDE [J].

BROWN, HC ;

CHOI, YM ;

NARASIMHAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3153-3163

[4]

CERNY M, 1969, COLLECT CZECH CHEM C, V34, P1025

[5] METHYLSULFINYL CARBANION (CH3-SO-CH2-) . FORMATION AND APPLICATIONS TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1345-+

[6] STUDIES IN STEREOCHEMISTRY .30. MODELS FOR STERIC CONTROL OF ASYMMETRIC INDUCTION [J].

CRAM, DJ ;

KOPECKY, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (11) :2748-2755

[7] ASYMMETRIC SYNTHESES BASED ON 1,3-OXATHIANES .1. SCOPE OF THE REACTION [J].

ELIEL, EL ;

MORRISNATSCHKE, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :2937-2942

[8] ORGANOSULFUR CHEMISTRY .2. HIGHLY STEREOSELECTIVE REACTIONS OF 1,3-DITHIANES - CONTRATHERMODYNAMIC FORMATION OF UNSTABLE DIASTEREOISOMERS [J].

ELIEL, EL ;

HARTMANN, AA ;

ABATJOGL.AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (06) :1807-1816

[9]

ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125

[10] ALKYLATION OF BETA-KETO SULFOXIDES . A GENERAL ROUTE TO KETONES [J].

GASSMAN, PG ;

RICHMOND, GD .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2355-&

← 1 2 →