Guanidine-copper complex catalyzed allylic borylation for the enantioconvergent synthesis of tertiary cyclic allylboronates

Guanidine-copper complex catalyzed allylic borylation for the enantioconvergent synthesis of tertiary cyclic allylboronates

An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine-copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed in...

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Bibliographic Details
Main Authors: Ge, Yicen, Cui, Xi-Yang, Tan, Siu Min, Jiang, Huan, Ren, Jingyun, Lee, Nicholas, Lee, Richmond, Tan, Choon-Hong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
Subjects:
Science::Chemistry
Asymmetric Catalysis
Borylation
Online Access:https://hdl.handle.net/10356/151801
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Institution: Nanyang Technological University
Language: English
Description
Summary:An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine-copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an SN 2' borylation process catalyzed by a monodentate guanidine-copper(I) complex that proceeds through a special direct enantioconvergent transformation mechanism.

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