TY - JOUR
T1 - Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide
AU - Takeuchi, Toshifumi
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
N1 - Funding Information:
This work was supported by JST, ACT-C (JPMJCR12YO), and KAKENHI (16K18856) from JSPS. This work was partially supported by JSPS KAKENHI Grant Number JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding. N.K. thanks the Naito Foundation for financial support. Dr. Tomoyuki Kimura at Institute of Microbial Chemistry and Dr. Hiroyasu Sato at Rigaku Corporation are gratefully acknowledged for assistance in the X-ray crystallographic analysis of 3c and 3n.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/5/18
Y1 - 2018/5/18
N2 - A direct catalytic asymmetric aldol addition of an α-vinyl 7-azaindoline amide to both aromatic and aliphatic aldehydes was promoted by a cooperative acid/base catalyst in a stereodivergent manner. The key structural element, a 7-azaindoline moiety, facilitated catalytic enolization, allowing for subsequent stereoselective aldol addition. Enantioselective synthesis of the key intermediate of blumiolide C and kainic acid supported the synthetic utility of this protocol.
AB - A direct catalytic asymmetric aldol addition of an α-vinyl 7-azaindoline amide to both aromatic and aliphatic aldehydes was promoted by a cooperative acid/base catalyst in a stereodivergent manner. The key structural element, a 7-azaindoline moiety, facilitated catalytic enolization, allowing for subsequent stereoselective aldol addition. Enantioselective synthesis of the key intermediate of blumiolide C and kainic acid supported the synthetic utility of this protocol.
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U2 - 10.1021/acs.joc.8b00743
DO - 10.1021/acs.joc.8b00743
M3 - Article
C2 - 29683326
AN - SCOPUS:85047318297
SN - 0022-3263
VL - 83
SP - 5851
EP - 5858
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -