PREPARATION OF ACYCLIC N-ACYL-N,O-ACETALS BY DECARBOXYLATION OF N-PROTECTED ALPHA-AMINO-ACIDS AND STUDIES OF ASYMMETRIC AMIDOALKYLATION WITH TRIMETHYLSILYL CYANIDE

被引:9
作者
HARDING, KE
LIU, LT
FARRAR, DG
COLEMAN, MT
TANSEY, SK
机构
[1] Department of Chemistry, Texas A&M University, TX 77843, College Station
基金
美国国家卫生研究院;
关键词
D O I
10.1080/00397919108021290
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative decarboxylation of N-acyl-alpha-amino acids with lead tetra-acetate followed by treatment with methanol provides a facile method for preparation of acyclic N-acyl-N,O-acetals, which can be used in asymmetric alpha-amidoalkylation reactions using trimethylsilyl cyanide as nucleophile.
引用
收藏
页码:1409 / 1417
页数:9
相关论文
共 36 条
[1]   NEW SYNTHESIS OF PIPECOLIC ACID AND ANALOGS [J].
ASHER, V ;
BECU, C ;
ANTEUNIS, MJO ;
CALLENS, R .
TETRAHEDRON LETTERS, 1981, 22 (02) :141-144
[2]   TOTAL SYNTHESES OF PENICILLANIC ACID S,S-DIOXIDE AND 6-AMINOPENICILLANIC ACID USING (BENZYLOXY)NITROMETHANE [J].
BARRETT, AGM ;
SAKADARAT, S .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5110-5117
[3]   STEREOCONTROLLED TOTAL SYNTHESIS OF THE CHIRAL BUILDING BLOCK (3S,4R)-3-[(R)-1-HYDROXYETHYL]-4-ACETYLOXY-AZETIDIN-2-ONE - A USEFUL SYNTHON FOR THE SYNTHESIS OF (+)-THIENAMYCIN, CARBAPENEMS AND PENEMS [J].
CAINELLI, G ;
CONTENTO, M ;
GIACOMINI, D ;
PANUNZIO, M .
TETRAHEDRON LETTERS, 1985, 26 (07) :937-940
[4]   CONVERSION OF ALPHA-AMINOCARBOXYLIC ACIDS TO ALPHA-AMINOPHOSPHONIC ACIDS [J].
CORCORAN, RC ;
GREEN, JM .
TETRAHEDRON LETTERS, 1990, 31 (47) :6827-6830
[5]   SELECTIVE MODIFICATION OF GLYCINE RESIDUES IN DIPEPTIDES [J].
EASTON, CJ ;
SCHARFBILLIG, IM ;
TAN, EW .
TETRAHEDRON LETTERS, 1988, 29 (13) :1565-1568
[6]   A STEREOSELECTIVE SYNTHESIS OF N-BOC-ALPHA-AMINO ALCOHOLS AND ALPHA-AMINO-ACIDS [J].
ERMERT, P ;
MEYER, J ;
STUCKI, C ;
SCHNEEBELI, J ;
OBRECHT, JP .
TETRAHEDRON LETTERS, 1988, 29 (11) :1265-1268
[7]   ELECTROCHEMICAL SYNTHESIS OF THE VINYLOGS OF N-ACYL N,O-ACETALS AND THEIR REACTIVITY [J].
FASSEUR, D ;
RIGO, B ;
CAULIEZ, P ;
DEBACKER, M ;
COUTURIER, D .
TETRAHEDRON LETTERS, 1990, 31 (12) :1713-1716
[8]   TRIMETHYLSILYL-SUBSTITUTED OPTICALLY-ACTIVE BETA-LACTAMS [J].
FRITZ, H ;
SUTTER, P ;
WEIS, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :558-561
[9]   ACYCLIC STEREOSELECTION IN ALPHA-AMIDOALKYLATION REACTIONS [J].
HARDING, KE ;
DAVIS, CS .
TETRAHEDRON LETTERS, 1988, 29 (16) :1891-1894
[10]  
HARDING KE, UNPUB