THE BENZOSTABASE PROTECTING GROUP FOR PRIMARY AMINES - APPLICATION TO ALIPHATIC-AMINES

被引：30
作者：
BONARLAW, RP
DAVIS, AP
DORGAN, BJ
REETZ, MT
WEHRSIG, A
机构：
[1] UNIV DUBLIN TRINITY COLL,DEPT CHEM,DUBLIN 2,IRELAND
[2] UNIV MARBURG,FACHBEREICH CHEM,W-3550 MARBURG,GERMANY
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 46期
关键词：
D O I：
10.1016/S0040-4039(00)97158-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The "benzostabase" (BSB) protecting group has been applied to primary aliphatic amines. It can be introduced via a dehydrogenative silylation employing an air- and moisture-stable reagent, and is appreciably more acid-stable than the related "stabase" group. BSB protection has been used in a stereoselective synthesis of amino-alcohols involving the addition of organometallic reagents to protected amino-aldehydes under "non-chelation control". © 1990.
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页码：6725 / 6728
页数：4
相关论文
共 8 条
[1]   A SIMPLE SYNTHESIS OF PRIMARY AMINES VIA THEIR N,N-BIS(TRIMETHYLSILYL) DERIVATIVES [J].
BESTMANN, HJ ;
WOLFEL, G .
CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (03) :1250-1254
[2]   SYNTHESIS OF STEROIDAL CYCLODIMERS FROM CHOLIC-ACID - A MOLECULAR FRAMEWORK WITH POTENTIAL FOR RECOGNITION AND CATALYSIS [J].
BONARLAW, RP ;
DAVIS, AP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (15) :1050-1052
[3]  
BONARLAW RP, COMMUNICATION
[4]   REACTIONS OF ORTHO-BIS(DIMETHYLSILYL)BENZENE WITH NITRILES CATALYZED BY RHODIUM COMPLEXES [J].
CORRIU, RJP ;
MOREAU, JJE ;
PATAUDSAT, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 228 (03) :301-308
[5]   SILICON IN SYNTHESIS - STABASE ADDUCTS - A NEW PRIMARY AMINE PROTECTING GROUP - ALKYLATION OF ETHYL GLYCINATE [J].
DJURIC, S ;
VENIT, J ;
MAGNUS, P .
TETRAHEDRON LETTERS, 1981, 22 (19) :1787-1790
[6]   The chemistry of the triethylsilicyl group [J].
Kraus, CA ;
Nelson, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :195-202
[7]  
Reetz M. T., 1987, ANGEW CHEM, V99, P1186
[8]   STEREOSELECTIVE SYNTHESIS OF BETA-AMINO ALCOHOLS FROM OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS [J].
REETZ, MT ;
DREWES, MW ;
SCHMITZ, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1141-1143
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