Affiliation:
1. Indian Institute of Technology Kharagpur 721302 Kharagpur West Bengal India
Abstract
AbstractThe highly stereoselective synthesis of a series of tetrasubstituted mono‐ as well as disilylated vinylboronates is reported by using the boron‐Wittig approach. The condensation between acylsilanes and gem‐diborylalkanes gave the desired tetrasubstituted olefins in good to excellent yield and high stereoselectivity. Also, a series of trisubstituted silylated vinyl MIDA‐boronates was synthesized by using the boron‐Wittig reaction followed by a transesterification reaction. This methodology allows direct incorporation of B(pin) and TMS groups in the anti‐position of the olefin in a highly stereoselective manner. Further, sequential Suzuki coupling reaction with the silylated vinyl boronic esters generated all‐carbon tetrasubstituted alkenes, which have been applied in the total synthesis of the anticancer drug Tamoxifen and aggregation‐induced luminogen agent TPE‐TF17.
Subject
General Chemistry,Catalysis,Organic Chemistry