Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways. Issue 40 (20th September 2021)

• Record Type: Journal Article
• Authors: Gao, Shang; Liu, Jiaming; Chen, Ming
• Is Part Of: Chemical science. Volume 12:Issue 40(2021)
• Page Start: 13398
• Page End: 13403
• Publication Date: 2021-09-20
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc04047b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We report herein catalytic asymmetric transformations of racemic α-borylmethyl-( E )-crotylboronate. Abstract : We report herein catalytic asymmetric transformations of racemic α-borylmethyl-( E )-crotylboronate. The Brønsted acid-catalyzed kinetic resolution–allylboration reaction sequence of the racemic reagent gave ( Z )-δ-hydroxymethyl- anti -homoallylic alcohols with high Z -selectivities and enantioselectivities upon oxidative workup. In parallel, enantioconvergent pathways were utilized to synthesize chiral nonracemic 1, 5-diols and α, β-unsaturated aldehydes with excellent optical purity.