TY - JOUR
T1 - Direct Catalytic Asymmetric Mannich-Type Reaction of Benzyl Isocyanide
T2 - Stereoselective Synthesis of 1,2-Diarylethylenediamines
AU - Tamura, Keiji
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
N1 - Funding Information:
This work was financially supported by JST, ACT-C, and KAKENHI (no. 25713002) from JSPS.
Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2015/5
Y1 - 2015/5
N2 - A direct catalytic asymmetric Mannich-type reaction of benzyl isocyanide using a CuI catalyst and N-(diphenylthiophosphinoyl)imines was developed. The simultaneous activation strategy by soft–soft interaction was the key to promote the reaction using a weakly acidic pronucleophile, benzyl isocyanide. The spontaneous cyclization of the Mannich adduct afforded the corresponding enantioenriched imidazolines, which could be precursors for a variety of 1,2-diarylethylenediamines.
AB - A direct catalytic asymmetric Mannich-type reaction of benzyl isocyanide using a CuI catalyst and N-(diphenylthiophosphinoyl)imines was developed. The simultaneous activation strategy by soft–soft interaction was the key to promote the reaction using a weakly acidic pronucleophile, benzyl isocyanide. The spontaneous cyclization of the Mannich adduct afforded the corresponding enantioenriched imidazolines, which could be precursors for a variety of 1,2-diarylethylenediamines.
KW - Asymmetric catalysis
KW - Chiral diamines
KW - Imidazoline
KW - Isocyanides
KW - Mannich reaction
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U2 - 10.1002/ejoc.201500336
DO - 10.1002/ejoc.201500336
M3 - Article
AN - SCOPUS:85027943756
SN - 0365-5490
VL - 2015
SP - 3026
EP - 3031
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
IS - 14
ER -