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A comparison of Diels-Alder catalysts generated from linear and vaulted biaryls and bromoborane-dimethylsulfide complex

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
36
Issue
19
Identifiers
DOI: 10.1016/0040-4039(95)00534-j

Abstract

Abstract Catalysts prepared from the vaulted biaryls 2 and 3 and bromoborane dimethylsulfide were compared with that generated from the linear biaryl 1 for their ability to provide enantioselective induction in the Diels-Alder reaction of cyclopentadiene and methacrolein. The fact that the S-enantiomers of 2 and 3 give opposite induction than the S-enantiomer of 1 and the fact that effective catalysts can not be generated from 1 and phenylboron dichloride suggests that the catalysts from 2 and 3 do not have the same structure as the C 3-symmetrical catalyst 4 produced from 1.

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