()-α-Boryl-crotylboron Reagents -selective Alkene Isomerization and Application to Stereoselective Syntheses of ()-δ-boryl--homoallylic Alcohols

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2019 Apr 19

PMID 30996958

Citations 16

Authors

Shang Gao

Jichao Chen

Ming Chen

Affiliations

Soon will be listed here.

Abstract

Stereoselective synthesis of ()-α-boryl-crotylboronate is developed. Ni-catalyzed -selective alkene isomerization of α-boryl substituted homoallylboronate provided the targeted ()-crotylboronate with high selectivity. Stereoselective addition of the novel crotylboron reagent to aldehydes gave ()-δ-boryl-substituted -homoallylic alcohols with excellent diastereoselectivities. The vinyl boronate unit in the products can be directly used for a subsequent C-C bond-forming transformation as illustrated in the synthesis of the C fragment of the natural products nannocystin A and nannocystin Ax.

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