TY - JOUR
T1 - Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides
AU - Sun, Zhongdong
AU - Sun, Bo
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
N1 - Funding Information:
This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (17H03025 and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS. N.K. thanks the Naito Foundation for financial support. We thank Dr. Tomoyuki Kimura at the Institute of Microbial Chemistry for assistance with the X-ray crystallography.
Funding Information:
This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (17H03025 and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/5/18
Y1 - 2018/5/18
N2 - Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides (p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.
AB - Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides (p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.
UR - http://www.scopus.com/inward/record.url?scp=85047358393&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85047358393&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.8b01109
DO - 10.1021/acs.orglett.8b01109
M3 - Article
C2 - 29722988
AN - SCOPUS:85047358393
VL - 20
SP - 3070
EP - 3073
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 10
ER -