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Synthesis of Chiral Bulky Monophosphite Ligands and Their Application in Cu-Catalyzed Asymmetric Conjugate Addition of Diethylzinc to Cyclic Enones

✍ Scribed by Bo WAN; Qinglu ZHAO; Lailai WANG

Book ID: 104452889
Publisher: Elsevier Science
Year: 2010
Weight: 285 KB
Volume: 31
Category: Article
ISSN: 1872-2067
DOI: 10.1016/s1872-2067(09)60063-2

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✦ Synopsis

A series of new bulky monophosphite ligands were synthesized from axially chiral BINOL and highly sterically hindered adamantanecarbonyl chloride. These ligands were applied to the Cu-catalyzed asymmetric 1,4-conjugate addition of diethylzinc to cyclic enones and were found to have moderate enantioselectivities (up to 61% ee). The stereochemically matched combination of (S)-BINOL in ligand (S)-(2-(adamantane-1-carboxylic acid)-1,1'-binapthalen-2'-yl)-((S)-1,1'-binaphthalen-2,2'-yl)phosphite induces a moderate enantioselectivity. The sense of enantioselectivity is mainly controlled by the configuration of the 2,2'-o,o-(1,1'-binaphthyl)-dioxo-phosphite moiety of the ligands.

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