Stereoselective production of β-amino alcohols and β-thioacyl alcohols via an application of the non-aldol aldol process

被引：13

作者：

Jung, ME ^{[1
]}

Sun, DQ ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 48期

关键词：

non-aldol aldol process; anti-aldol products; beta-amino and beta-thioacyl alcohols;

D O I：

10.1016/S0040-4039(99)01786-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mesylates used as protecting groups to permit the formation of bis(polypropionates) via the nonaldol aldol process can be easily displaced with good nucleophiles, e.g., azide, thioacetate, acetate, to generate beta-azido (and beta-amino) alcohols, beta-thioacyl alcohols, and aldols of the opposite chirality, e.g.,syn isomers afford anti products. Thus the anti mesylate 15 affords the all-anti mzido aldol system 16 in good yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8343 / 8346

页数：4

共 9 条

[1] A SELECTIVE AND EFFICIENT DEMESYLATION USING METHYLMAGNESIUM BROMIDE [J].

COSSY, J ;

RANAIVOSATA, JL ;

BELLOSTA, V ;

WIETZKE, R .

SYNTHETIC COMMUNICATIONS, 1995, 25 (20) :3109-3112

[2] ENANTIOSPECIFIC SYNTHESIS OF ALL 4 DIASTEREOMERS OF 2-METHYL-3-((TRIALKYLSILYL)OXY)ALKANALS - FACILE PREPARATION OF ALDOLS BY NON-ALDOL CHEMISTRY [J].

JUNG, ME ;

DAMICO, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (25) :12208-12209

[3] Stereospecific formation of optically active 5-alkyl-4-methyl-3-[(trialkylsilyl)oxy]-2-([(trialkylsilyl)oxy]-methyl)tetrahydrofurans via diastereoselective epoxidation and rearrangement of 5-[(trialkylsilyl)oxy]-2-alken-1-ols [J].

Jung, ME ;

D'Amico, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12150-12158

[4] Synthesis of four diastereomeric 3,5-dialkoxy-2,4-dimethylalkanals by a simple extension of the non-aldol aldol process to bis(propionates) [J].

Jung, ME ;

Lee, WS ;

Sun, DQ .

ORGANIC LETTERS, 1999, 1 (02) :307-309

[5] Conversion of homoallylic alcohols with alkene protection to the corresponding methyl ketones [J].

Jung, ME ;

Karama, U ;

Marquez, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :663-665

[6] Rearrangement of epoxides in non-aldol aldol process: Allylic vs. tertiary and secondary carbocationic centers [J].

Jung, ME ;

Marquez, R .

TETRAHEDRON LETTERS, 1999, 40 (16) :3129-3132

[7] Stereospecific rearrangements of optically active 2-aryl-3-ethenyloxiranes to give optically active beta-ethenylbenzeneethanols: Benzyl vs. allyl cations and an efficient synthesis of (S)-ibuprofen [J].

Jung, ME ;

Anderson, KL .

TETRAHEDRON LETTERS, 1997, 38 (15) :2605-2608

[8] STEREOSPECIFIC REARRANGEMENT OF OPTICALLY-ACTIVE TERTIARY ALLYLIC EPOXIDES TO GIVE OPTICALLY-ACTIVE QUATERNARY ALDEHYDES - SYNTHESIS OF ALPHA-ALKYL AMINO ALDEHYDES AND ACIDS [J].

JUNG, ME ;

DAMICO, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7379-7388

[9] TEDANOLIDE - A POTENT CYTO-TOXIC MACROLIDE FROM THE CARIBBEAN SPONGE TEDANIA-IGNIS [J].

SCHMITZ, FJ ;

GUNASEKERA, SP ;

YALAMANCHILI, G ;

HOSSAIN, MB ;

VANDERHELM, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :7251-7252

← 1 →