CRCL2 MEDIATED ALLYLATION OF N-PROTECTED ALPHA-AMINO ALDEHYDES - A VERSATILE SYNTHESIS OF POLYPEPTIDES CONTAINING AN HYDROXYETHYLENE ISOSTERE

被引：38

作者：

CIAPETTI, P ^{[1
]}

TADDEI, M ^{[1
]}

ULIVI, P ^{[1
]}

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN UGO SCHIFF,I-50121 FLORENCE,ITALY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)76862-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Differently substituted allylic bromides react with N-protected amino aldehydes to give intermediate products for the synthesis of hydroxyethylene dipeptide isosteres. The low stereoselectivity of this reaction can be improved using aldehydes protected with hindered groups. This reaction can be efficiently applied to oligopetide aldehydes. We describe a protocol, for the preparation of peptides containing an hydroxyethylene isostere, which allows a rapid variations of the aminoacid sequence

引用

页码：3183 / 3186

页数：4

共 33 条

[1] Zinc-mediated allylation of N-protected alpha-amino aldehydes in aqueous solution. Stereoselective synthesis of Phe-Phe hydroxyethylene dipeptide isosteres
Hanessian, S
Park, H
Yang, RY
SYNLETT, 1997, (04) : 351 - +
[2] CONFIGURATIONAL STABILITY OF N-PROTECTED ALPHA-AMINO ALDEHYDES
LUBELL, WD
RAPOPORT, H
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) : 236 - 239
[3] SYNTHESIS OF CHIRAL N-PROTECTED ALPHA-AMINO ALDEHYDES BY REDUCTION OF N-PROTECTED N-CARBOXYANHYDRIDES (UNCAS)
FEHRENTZ, JA
POTHION, C
CALIFANO, JC
LOFFET, A
MARTINEZ, J
TETRAHEDRON LETTERS, 1994, 35 (48) : 9031 - 9034
[4] AN EFFICIENT METHOD FOR PREPARATION OF OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES FROM N-PROTECTED ALPHA-AMINO ALCOHOLS
SOUCEK, M
URBAN, J
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1995, 60 (04) : 693 - 696
[5] CrCl2 mediated addition of allylic halides or phosphates to N-protected alpha-amino aldehydes. Stereocontrolled synthesis of a new core for C-2 symmetric HIV-protease inhibitors.
Ciapetti, P
Falorni, M
Taddei, M
TETRAHEDRON, 1996, 52 (21) : 7379 - 7390
[6] OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES IN ORGANIC-SYNTHESIS
JURCZAK, J
GOLEBIOWSKI, A
CHEMICAL REVIEWS, 1989, 89 (01) : 149 - 164
[7] alpha-amino acids and N-protected alpha-amino aldehydes by stereoselective additions of a chiral vinyllithium reagent to sulfonylimines
Braun, M
Opdenbusch, K
LIEBIGS ANNALEN-RECUEIL, 1997, (01): : 141 - 154
[8] ORGANOCERIUM ADDITIONS TO CHIRAL ALPHA,ALPHA-DIALKOXY HYDRAZONES - ASYMMETRIC-SYNTHESIS OF N-PROTECTED ALPHA-AMINO ACETALS AND ALPHA-AMINO ALDEHYDES
DENMARK, SE
NICAISE, O
SYNLETT, 1993, (05) : 359 - 361
[9] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS AND N-PROTECTED ALPHA-AMINO ALDEHYDES BY ADDITION OF CHIRAL VINYL ANIONS TO SULFONYLIMINES
BRAUN, M
OPDENBUSCH, K
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04): : 578 - 580
[10] Zinc-mediated allylation of N-protected alpha-amino aldehydes in aqueous solution. Stereoselective synthesis of anti- and syn-beta-amino alcohols with functionalized allyl groups
Hanessian, S
Park, H
Yang, RY
SYNLETT, 1997, (04) : 353 - &

← 1 2 3 4 →