Section 12
Chapter 11,304

Rhodium-catalyzed asymmetric arylation of alpha,beta-unsaturated imines with arylstannanes. Catalytic asymmetric synthesis of allylic amines

Hayashi, T.; Ishigedani, M.

Tetrahedron 57(13): 2589-2595, 26 March


ISSN/ISBN: 0040-4020
Accession: 011303193

Catalytic asymmetric arylation of N-alkylidenesulfonamides 1a-d, which are prepared from alpha,beta-unsaturated aldehydes and 4-nitrobenzenesulfonamide, with aryltrimethylstannanes 2m-p proceeded in the presence of 3 mol% of a rhodium catalyst coordinated with (R)-MOP ligand in dioxane at 110degreeC to give sulfonamide of allylic amines (R)-3 with high enantioselectivity (up to 96% ee) in high yields. Some of the allylic amines were converted in to the sulfonamide of (S)-phenylglycine without loss of enantiomeric purity by oxidative cleavage of the carbon-carbon double bond.

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