Enantioselective Binaphthophosphepine‐Promoted [3+2] Annulations of  N ‐Ts‐ and  N ‐DPP‐Imines with Allenoates and 2‐Butynoates | Zendy

Pinto Nathalie | Zendy; FleuryBrégeot Nicolas | Zendy; Marinetti Angela | Zendy

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Enantioselective Binaphthophosphepine‐Promoted [3+2] Annulations of N ‐Ts‐ and N ‐DPP‐Imines with Allenoates and 2‐Butynoates

Author(s) -

Pinto Nathalie,

FleuryBrégeot Nicolas,

Marinetti Angela

Publication year - 2009

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.200800598

Subject(s) - chemistry , enantioselective synthesis , imine , enantiomer , reactivity (psychology) , catalysis , enantiomeric excess , medicinal chemistry , organic chemistry , stereochemistry , combinatorial chemistry , medicine , alternative medicine , pathology

The use of binaphthophosphepine 1a as a catalyst for the [3+2] cyclisation between allenoates or 2‐butynoates andimines was investigated. The effects of the imine protecting group on both the catalytic activity and enantioselectivity were determined by comparing the behaviour of N ‐tosyl‐ and N ‐DPP‐imines. The N ‐DPP‐imines displayed lower reactivity, but afforded the desired pyrrolines in higher enantiomeric excess (73–92 % ee ). The DPP protecting group was removed from the final pyrrolines under mild conditions to afford the corresponding secondary amines. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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