Development of α, α-disubstituted crotylboronate reagents and stereoselective crotylation via Brønsted or Lewis acid catalysis

S Gao, M Duan, Q Shao, KN Houk… - Journal of the American …, 2020 - ACS Publications
The development of α, α-disubstituted crotylboronate reagents is reported. Chiral Brønsted
acid-catalyzed asymmetric aldehyde addition with the developed E-crotylboron reagent …

Copper-catalyzed highly selective hydrosilylation of silyl or boryl alkene: a method for preparing chiral geminated disilyl and borylsilyl reagents

M Zhang, Y Ji, Z Zhang, C Zhang - Organic Letters, 2022 - ACS Publications
The copper-catalyzed highly selective hydrosilylation of silyl or boryl alkene has been
developed. This chemistry could afford a practical method for preparing chiral geminated …

Iterative assembly line synthesis of polypropionates with full stereocontrol

T Bootwicha, JM Feilner, EL Myers, VK Aggarwal - Nature Chemistry, 2017 - nature.com
The polypropionate motif is ubiquitous, being characteristic of the most important family of
natural products for human health, the polyketides. Numerous strategies have been devised …

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

T Miura, J Nakahashi, W Zhou, Y Shiratori… - Journal of the …, 2017 - ACS Publications
A cationic ruthenium (II) complex catalyzes double-bond transposition of 1, 1-di (boryl) alk-3-
enes to generate in situ 1, 1-di (boryl) alk-2-enes, which then undergo chiral phosphoric acid …

Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid

T Miura, J Nakahashi… - Angewandte Chemie …, 2017 - Wiley Online Library
Abstract (E)‐δ‐Boryl‐substituted anti‐homoallylic alcohols are synthesized in a highly
diastereo‐and enantioselective manner from 1, 1‐di (boryl) alk‐3‐enes and aldehydes …

Iterative Catalyst-Controlled Diastereoselective Matteson Homologations Enable the Selective Synthesis of Benzestrol Isomers

SR Angle, HA Sharma, CK Choi… - Journal of the …, 2024 - ACS Publications
We report the development of an iterative Matteson homologation reaction with catalyst-
controlled diastereoselectivity through the design of a new catalyst. This reaction was …

Stereochemical control via chirality pairing: stereodivergent syntheses of enantioenriched homoallylic alcohols

S Gao, M Duan, J Liu, P Yu, KN Houk… - Angewandte …, 2021 - Wiley Online Library
We report herein the development of stereodivergent syntheses of enantioenriched
homoallylic alcohols using chiral nonracemic α‐CH2Bpin‐substituted crotylboronate. Chiral …

Chiral Phosphoric Acid Dual‐Function Catalysis: Asymmetric Allylation with α‐Vinyl Allylboron Reagents

S Gao, M Duan, KN Houk… - Angewandte Chemie …, 2020 - Wiley Online Library
We report a dual function asymmetric catalysis by a chiral phosphoric acid catalyst that
controls both enantioselective addition of an achiral α‐vinyl allylboronate to aldehydes and …

(Z)-α-Boryl-crotylboron reagents via Z-selective alkene isomerization and application to stereoselective syntheses of (E)-δ-boryl-syn-homoallylic alcohols

S Gao, J Chen, M Chen - Chemical Science, 2019 - pubs.rsc.org
Stereoselective synthesis of (Z)-α-boryl-crotylboronate is developed. Ni-catalyzed Z-
selective alkene isomerization of α-boryl substituted homoallylboronate provided the …

Chemo- and Stereoselective Crotylation of Aldehydes and Cyclic Aldimines with Allylic gem-Diboronate Ester

J Park, S Choi, Y Lee, SH Cho - Organic letters, 2017 - ACS Publications
We report a highly chemo-and stereoselective crotylation of aldehydes and cyclic aldimines
with allylic-gem-diboronate ester as a new type of organoboron reagent. The allylic-gem …