Pd-Catalyzed Allylic Alkylation of gem-Alkyl,Aryl-Disubstituted Allyl Reagents with Ketones: Diastereoselective Construction of Vicinal Tertiary and Quaternary Carbon Centers,ACS Catalysis

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Pd-Catalyzed Allylic Alkylation of gem-Alkyl,Aryl-Disubstituted Allyl Reagents with Ketones: Diastereoselective Construction of Vicinal Tertiary and Quaternary Carbon Centers
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-03-16 00:00:00 , DOI: 10.1021/acscatal.7b04313
Fei-Le Yu ₁ , Da-Chang Bai _{1,

2} , Xiu-Yan Liu ₁ , Yang-Jie Jiang _{1,

3} , Chang-Hua Ding ₁ , Xue-Long Hou _{1,

4}

Affiliation

(E)-gem-Alkyl,aryl-disubstituted allyl carbonates can react with ketones under Pd catalysis using a commercially available NHC ligand by suppressing the β-H elimination. Ketones with α-tertiary, β-quaternary carbon stereocenters were produced in high yields with high regio- and diastereoselectivities. Kinetic resolution of the reaction product via CBS reduction afforded the optically active ketone as well as the alcohol with high enantioselectivity (S-factor = 35). The utility of the methodology was also demonstrated by transformations of the reaction products.

中文翻译：

的钯催化的烯丙基烷基化偕烷基，芳基二取代烯丙基试剂与酮：邻位第三的立体选择性建设和季碳中心

（E）-宝石-烷基，芳基-二取代的碳酸烯丙酯可以通过抑制β-H的消除，在Pd催化下，使用市售的NHC配体与酮反应。具有高产，高区域选择性和非对映选择性的具有α-叔，β-季碳立体中心的酮。通过CBS还原反应产物的动力学拆分提供了光学活性的酮以及具有高对映选择性的醇（S-因子＝ 35）。通过反应产物的转化也证明了该方法的实用性。

更新日期：2018-03-16

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