Direct Catalytic Asymmetric Mannich‐Type Reaction of Benzyl Isocyanide: Stereoselective Synthesis of 1,2‐Diarylethylenediamines | Zendy

Tamura Keiji | Zendy; Kumagai Naoya | Zendy; Shibasaki Masakatsu | Zendy

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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.

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