Premium
Catalytic Asymmetric 1,4‐Addition Reactions of Simple Alkylnitriles
Author(s) -
Yamashita Yasuhiro,
Sato Io,
Suzuki Hirotsugu,
Kobayashi Shū
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500405
Subject(s) - catalysis , chemistry , crown ether , ether , addition reaction , enantioselective synthesis , potassium , combinatorial chemistry , organic chemistry , ion
The development of catalytic asymmetric carbon–carbon bond‐forming reactions of alkylnitriles that do not have an activating group at the α‐position, under proton‐transfer conditions, is a challenging research topic. Here, we report catalytic asymmetric direct‐type 1,4‐addition reactions of alkylnitriles with α,β‐unsaturated amides by using a catalytic amount of potassium hexamethyldisilazide (KHMDS) with a chiral macro crown ether. The desired reactions proceeded in high yields with good diastereo‐ and enantioselectivities. To our knowledge, this is the first example of catalytic asymmetric direct‐type 1,4‐addition reaction of alkylnitriles without any activating group at the α‐position.