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Cobalt-Mediated, Enantioselective Synthesis of C-2 and C-1 Dienes

Boyd, WC; Crimmin, MR; Rosebrugh, LE; Schomaker, JM; Bergman, RG; Toste, FD; (2010) Cobalt-Mediated, Enantioselective Synthesis of C-2 and C-1 Dienes. J AM CHEM SOC , 132 (46) 16365 - 16367. 10.1021/ja107968c.

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Abstract

The asymmetric C-H functionalization of norbornene and norbornadiene with five-, six-, and seven-membered cyclicenones mediated by the reactive intermediate [{eta(5)-((BuMe2Si)-Bu-1)C5H4}Co(NO)(2)] is reported. A novel base mixture derived from enantiopure ammonium salts and NaHMDS was used as a source of chirality, and this enantioselective desymmetrization of C-s alkenes has been applied to the asymmetric synthesis of G(2)- and C-1-symmetric diene ligands in high regioselectivity (3.7-20:1 anti/syn), near perfect diastereoselectivity (>99:1 dr), and high enantioselectivity (90-96% ee).

Type:Article
Title:Cobalt-Mediated, Enantioselective Synthesis of C-2 and C-1 Dienes
DOI:10.1021/ja107968c
Keywords:CATALYZED ASYMMETRIC 1,4-ADDITION, NITROSYL METAL-COMPLEXES, ORGANOCOBALT COMPOUNDS, CONJUGATE ADDITIONS, ARYLBORONIC ACIDS, CHIRAL LIGANDS, NITRIC-OXIDE, OLEFINS, FUNCTIONALIZATION, ALKENES
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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