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Cu-catalyzed asymmetric conjugate reduction of β-substituted α,β-unsaturated phosphonates: an efficient synthesis of optically active β-stereogenic alkylphosphonates

✍ Scribed by Zheng-Chao Duan; Xiang-Ping Hu; Dao-Yong Wang; Sai-Bo Yu; Zhuo Zheng

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 249 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.09.094

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✦ Synopsis

A series of chiral alkylphosphonates bearing b-stereogenic center were synthesized in good enantioselectivities (up to 95% ee) via the CuH-catalyzed asymmetric conjugate reduction of b-substituted a,b-unsaturated phosphonates under optimal conditions using Cu(OAc) 2 ÁH 2 O as the copper source, (R)-SEGPHOS as the ligand, PMHS as the siloxane, and t-BuOH as the additive.

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