Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide

被引：57

作者：

Benedetti, F ^{[1
]}

Berti, F ^{[1
]}

Norbedo, S ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 43期

关键词：

aluminium and compounds; azides; epoxides; isosteres;

D O I：

10.1016/S0040-4039(98)01733-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,3-Epoxyalcohols react with diethylaluminium azide under mild conditions to give 3-azido-1,2-diols resulting from the regio- and stereoselective attack of the nucleophile at the epoxide C-3. The high regioselectivity (>25:1) observed with both cis and trans substituted epoxides is not affected by bulky substituents at C-3. The method has been successfully applied also to the synthesis of diaminodiol dipeptide isosteres, (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7971 / 7974

页数：4

共 20 条

[1] BENEDETTI F, 1997, J ORG CHEM, V62, P9349
[2] A convenient synthesis of 1-(S)-[1'-(S)-(t-butyloxycarbonylamino)-2'-phenylethyl]oxirane. A useful building block in the synthesis of HIV protease inhibitors.
Branalt, J
Kvarnstrom, I
Classon, B
Samuelsson, B
Nillroth, U
Danielson, UH
Karlen, A
Hallberg, A
[J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3483 - 3486
[3] CARON M, 1988, J ORG CHEM, V53, P5187
[4] A NEW SYNTHESIS FOR ALKYLMETAL AZIDES
DEHNICKE, K
STRAHLE, J
SEYBOLD, D
MULLER, J
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 6 (03) : 298 - &
[5] Jurczak J., 1997, PREPARATIVE CARBOHYD, P595
[6] DISCOVERY OF A PEPTIDE-BASED RENIN INHIBITOR WITH ORAL BIOAVAILABILITY AND EFFICACY
KLEINERT, HD
ROSENBERG, SH
BAKER, WR
STEIN, HH
KLINGHOFER, V
BARLOW, J
SPINA, K
POLAKOWSKI, J
KOVAR, P
COHEN, J
DENISSEN, J
[J]. SCIENCE, 1992, 257 (5078) : 1940 - 1943
[7] ASYMMETRIC EPOXIDATION OF ALLYL ALCOHOL - EFFICIENT ROUTES TO HOMOCHIRAL BETA-ADRENERGIC BLOCKING-AGENTS
KLUNDER, JM
KO, SY
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) : 3710 - 3712
[8] RENIN INHIBITORS - DIPEPTIDE ANALOGS OF ANGIOTENSINOGEN UTILIZING A DIHYDROXYETHYLENE TRANSITION-STATE MIMIC AT THE SCISSILE BOND TO IMPART GREATER INHIBITORY POTENCY
LULY, JR
BAMAUNG, N
SODERQUIST, J
FUNG, AKL
STEIN, H
KLEINERT, HD
MARCOTTE, PA
EGAN, DA
BOPP, B
MERITS, I
BOLIS, G
GREER, J
PERUN, TJ
PLATTNER, JJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) : 2264 - 2276
[9] A HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE RING-OPENING OF 2,3-EPOXY ALCOHOLS WITH TRIMETHYLSILYL AZIDE-DIETHYLALUMINUM FLUORIDE SYSTEM
MARUOKA, K
SANO, H
YAMAMOTO, H
[J]. CHEMISTRY LETTERS, 1985, (05) : 599 - 602
[10] MEREYALA HB, 1986, HELV CHIM ACTA, V69, P415

← 1 2 →