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Copper‐Catalyzed Tandem Hydrocupration and Diastereo‐ and Enantioselective Borylalkyl Addition to Aldehydes
Author(s) -
Jang Won Jun,
Yun Jaesook
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201806937
Subject(s) - stereocenter , enantioselective synthesis , electrophile , chemistry , stereoselectivity , catalysis , tandem , yield (engineering) , copper , alkyl , aldehyde , organic chemistry , combinatorial chemistry , stereoisomerism , cascade reaction , boron , materials science , metallurgy , composite material
We report the copper‐catalyzed stereoselective addition of in situ generated chiral boron‐α‐alkyl intermediates to various aldehydes including α,β‐unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2‐hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo‐ and enantioselectivity up to a ratio greater than 98:2. In particular, α,β‐unsaturated aldehydes were successfully used as electrophiles in Cu−H catalysis through 1,2‐addition without significant reduction. The resulting 1,2‐hydroxyboronates were used in various transformations.