TY - JOUR
T1 - Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides
AU - Arteaga, Fernando Arteaga
AU - Liu, Zijian
AU - Brewitz, Lennart
AU - Chen, Jianyang
AU - Sun, Bo
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
N1 - Funding Information:
This work was financially supported by JST, ACT-C (for M.S.), and KAKENHI (No. 25713002) from JSPS (for N.K.). N.K. thanks The Naito Foundation for financial support. Dr. Ryuichi Sawa, Ms. Yumiko Kubota, and Dr. Kiyoko Iijima at the Institute of Microbial Chemistry are gratefully acknowledged for their assistance with the NMR analysis. We thank Dr. Tomoyuki Kimura at the Institute of Microbial Chemistry for assistance with the X-ray crystallography.
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/5/20
Y1 - 2016/5/20
N2 - Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.
AB - Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.
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U2 - 10.1021/acs.orglett.6b00879
DO - 10.1021/acs.orglett.6b00879
M3 - Article
AN - SCOPUS:84971334396
SN - 1523-7060
VL - 18
SP - 2391
EP - 2394
JO - Organic Letters
JF - Organic Letters
IS - 10
ER -