trans-2-Tritylcyclohexanol as a Chiral Auxiliary in Permanganate-Mediated Oxidative Cyclization of 2-Methylenehept-5-enoates: Application to the Synthesis of trans-(+)-Linalool Oxide

被引：17

作者：

Al Hazmi, Ali M. ^{[1
]}

Sheikh, Nadeem S. ^{[1
]}

Bataille, Carole J. R. ^{[1
]}

Al-Hadedi, Azzam A. M. ^{[1
]}

Watkin, Sam V. ^{[1
]}

Luker, Tim J. ^{[2
]}

Camp, Nicholas P. ^{[3
]}

Brown, Richard C. D. ^{[1
]}

机构：

[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

[2] AstraZeneca R&D Charnwood, Loughborough LE11 5RH, Leics, England

[3] Eli Lilly Res Ctr UK, Windlesham GU20 6PH, Surrey, England

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 19期

基金：

英国工程与自然科学研究理事会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC INDUCTION; CONVENIENT SYNTHESIS; CONJUGATE ADDITION; DIELS-ALDER; LINALYL; STEREOCHEMISTRY; CONSTRUCTION;

D O I：

10.1021/ol502454r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (d(r) similar to 97:3). Chiral resolution of (+/-)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.

引用

页码：5104 / 5107

页数：4

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