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Asymmetric Wittig reactions of chiral arsonium ylides. Part 2: Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides

✍ Scribed by Wei-Min Dai; Chi Wai Lau

Book ID: 104230267
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 103 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00193-9

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✦ Synopsis

Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides with chiral ligand-derived stable arsonium ylides proceeded in a kinetic resolution manner. The (E)-olefin products were obtained in excellent chemical yields and in up to 88:12 diastereoselectivity. Effects of the amide alkyl groups, metal counter ions and solvents on the diastereoselectivity were investigated.

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