A HIGHLY STEREOSELECTIVE CONVERSION OF ALPHA-ALLENIC ALCOHOLS TO 1,2-SYN AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION

被引：26

作者：

FRIESEN, RW

机构：

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)97592-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodocarbamation of α-allenic alcohol O-carbamates is described. Reactions carried out in anhydrous Et2O are highly diastereoselective, providing the cyclic carbamates trans-8 and cis-9 in ratios ranging from 21:1 to >99:<1. Hydrolysis and acetylation provide the corresponding amino alcohol derivatives syn-10 and anti-11. © 1990.

引用

收藏

页码：4249 / 4252

页数：4

相关论文

共 23 条

[1] CYCLIZATION OF GAMMA-ALLENIC AND DELTA-ALLENIC AMINES - SYNTHESIS OF 2-ALCENYL PYRROLIDINES AND 2-ALCENYL PIPERIDENES [J].

ARSENIYADIS, S ;

GORE, J .

TETRAHEDRON LETTERS, 1983, 24 (37) :3997-4000

[2] REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF EPOXY ALCOHOLS AND TRIOLS FROM ALLYLIC AND HOMOALLYLIC ALCOHOLS VIA IODO CARBONATES [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4626-4633

[3] A NEW SYNTHETIC APPROACH TO 3-AMINO-1,2-DIOLS FROM ALLYLIC ALCOHOLS VIA TRICHLOROACETIMIDATES [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (24) :1489-1490

[4] STEREOCONTROLLED REACTIONS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S .

PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1679-1688

[5] A REGIOSELECTIVE INTRODUCTION OF FUNCTIONAL-GROUPS TO THE DOUBLE-BONDS OF ALLYLIC AND HOMOALLYLIC ALCOHOLS VIA THE CORRESPONDING TRICHLOROACETIMIDATES [J].

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (22) :1308-1309

[6] OXAZOLIDIN-2-ONES FROM ALLYLIC AMINES BY MEANS OF IODINE AND CARBONATE ANION ON POLYMERIC SUPPORT - A CONVENIENT SYNTHESIS OF (+/-)-PROPRANOLOL [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :713-717

[7] A NEW REGIO-SELECTIVE AND STEREO-SELECTIVE FUNCTIONALIZATION OF ALLYLIC AND HOMOALLYLIC ALCOHOLS [J].

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (10) :465-466

[8]

CARDILLO G, 1985, TETRAHEDRON, V41, P167

[9] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].

CHAMBERLIN, AR ;

MULHOLLAND, RL ;

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677

[10]

CHILOT JJ, 1984, B SOC CHIM FR II-CH, P307