Neighbouring group assisted sulfonamide cleavage of sharpless aminols under acetonation conditions

被引：38

作者：

Chandrasekhar, S ^{[1
]}

Mohapatra, S ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)10638-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is accidentally observed that N-Ts cleavage and simultaneous protection of resulting free amino group as acetonide with the adjacent hydroxy group is achieved in one pot. Neighbouring carboxylic ester group is essential for this transformation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：695 / 698

页数：4

共 14 条

[1] PROTECTION OF AMINES BY THE PYRIDINE-2-SULFONYL GROUP AND ITS CLEAVAGE UNDER MILD CONDITIONS (SMI2 OR ELECTROLYSIS) [J].

GOULAOUICDUBOIS, C ;

GUGGISBERG, A ;

HESSE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5969-5972

[2] SYNTHESIS AND SELECTIVE DEPROTECTION OF THE PENTA-N-PROTECTED POLYAMINE 1,16-DIAMINO-4,8,13-TRIAZAHEXADECANE [J].

GOULAOUICDUBOIS, C ;

GUGGISBERG, A ;

HESSE, M .

TETRAHEDRON, 1995, 51 (46) :12573-12582

[3] CLEAVAGE OF SULFONAMIDES WITH SODIUM NAPHTHALENE [J].

JI, S ;

GORTLER, LB ;

WARING, A ;

BATTISTI, A ;

BANK, S ;

CLOSSON, WD ;

WRIEDE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5311-&

[4] DISCOVERY OF A PEPTIDE-BASED RENIN INHIBITOR WITH ORAL BIOAVAILABILITY AND EFFICACY [J].

KLEINERT, HD ;

ROSENBERG, SH ;

BAKER, WR ;

STEIN, HH ;

KLINGHOFER, V ;

BARLOW, J ;

SPINA, K ;

POLAKOWSKI, J ;

KOVAR, P ;

COHEN, J ;

DENISSEN, J .

SCIENCE, 1992, 257 (5078) :1940-1943

[5]

Knowles H, 1997, SYNLETT, P271

[6] N-halocarbamate salts lead to more efficient catalytic asymmetric aminohydroxylation [J].

Li, GG ;

Angert, HH ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2813-2817

[7] Catalytic asymmetric aminohydroxylation (AA) of olefins [J].

Li, GG ;

Chang, HT ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :451-454

[8]

NISHIMURA O, 1976, CHEM PHARM BULL, V24, P1568

[9] Mild, efficient cleavage of arenesulfonamides by magnesium reduction [J].

Nyasse, B ;

Grehn, L ;

Ragnarsson, U .

CHEMICAL COMMUNICATIONS, 1997, (11) :1017-1018

[10] A radical approach to N-desulfonylation [J].

Parsons, AF ;

Pettifer, RM .

TETRAHEDRON LETTERS, 1996, 37 (10) :1667-1670

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