Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation |
| |
Authors: | Naoyoshi Maezaki Suguru YagiShizuka Ohsawa Hirofumi OhishiTetsuaki Tanaka |
| |
Institution: | a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan b Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan |
| |
Abstract: | Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-β-sulfinyl α,β-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. |
| |
Keywords: | sulfoxides asymmetric reaction palladium catalyst sulfinylzincation |
本文献已被 ScienceDirect 等数据库收录! |
|