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Direct Catalytic Asymmetric Mannich‐Type Reaction of Benzyl Isocyanide: Stereoselective Synthesis of 1,2‐Diarylethylenediamines
Author(s) -
Tamura Keiji,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500336
Subject(s) - chemistry , isocyanide , catalysis , stereoselectivity , adduct , mannich reaction , combinatorial chemistry , organic chemistry , medicinal chemistry
A direct catalytic asymmetric Mannich‐type reaction of benzyl isocyanide using a Cu I 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.