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Enantio‐ and Diastereoselective Cyclopropanation of 1‐Alkenylboronates: Synthesis of 1‐Boryl‐2,3‐Disubstituted Cyclopropanes
Author(s) -
Carreras Javier,
Caballero Ana,
Pérez Pedro J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710415
Subject(s) - cyclopropanation , ethyl diazoacetate , hydroboration , chemistry , catalysis , organic chemistry , combinatorial chemistry , stereochemistry
A novel, highly enantio‐ and diastereoselective synthesis of 1‐boryl‐2,3‐disubstituted cyclopropanes has been developed by means of the cyclopropanation of alkenylboronates with ethyl diazoacetate in the presence of catalytic amounts of a chiral copper(I) complex. The products can also be directly accessed from alkynes through an operationally simple, sequential hydroboration–cyclopropanation protocol. The resulting enantioenriched 1‐boryl‐2,3‐disubstituted cyclopropanes are versatile synthetic intermediates that undergo further transformations at the carbon–boron bond.