Catalytic asymmetric synthesis of chiral allylic esters
Catalytic asymmetric synthesis of chiral allylic esters
复制标题
DOI：
10.1021/ja0425583
复制
发表时间：
2005-03-09
影响因子：
15
通讯作者：
Overman, LE
中科院分区：
文献类型：
--
作者：
Kirsch, SF;Overman, LE
前手性 (Z)-2-烯-1-醇的三氯乙酰亚胺酯衍生物在室温下与羧酸反应，在存在以下物质的情况下生成高对映体纯度的手性 3-酰氧基-1-烯二-μ-乙酰双[(η5-(S)-(pR)-2-(2'-(4'-甲基乙基)恶唑啉基)环戊二烯基,1-C,3'-N)(η4-四苯基环丁二烯)钴]二钯(COP-OAc)或其对映体。该反应具有广泛的范围，以可预测的高立体诱导进行，在室温下使用高底物浓度和低催化剂负载完成，并且可能通过新颖的机制进行。
Trichloroacetimidate derivatives of prochiral (Z)-2-alken-1-ols react at room temperature with carboxylic acids to give chiral 3-acyloxy-1-alkenes in high enantiopurity in the presence of di-μ-acetatobis[(η5-(S)-(pR)-2-(2‘-(4‘-methylethyl)oxazolinyl)cyclopentadienyl,1-C,3‘-N)(η4-tetraphenylcyclobutadiene)cobalt]dipalladium (COP-OAc) or its enantiomer. This reaction has broad scope, proceeds with predictable high stereoinduction, is accomplished at room temperature using high substrate concentrations and low catalyst loadings, and likely proceeds by a novel mechanism.