Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 47, Pages 17082-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja908571w
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- JSPS
- Grants-in-Aid for Scientific Research [20685008] Funding Source: KAKEN
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Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol. reaction of a-substituted a-isothiocyanato esters with unactivated simple ketones is described. A Bu2Mg/Schiff base catalyst promoted the aldol addition/cyclization sequence at room temperature, giving protected alpha-amino-beta-hydroxy esters with contiguous tetrasubstituted chiral carbon stereocenters in 99 to 68% yield, 98:2 to 74:26 dr, and 98 to 82% ee.
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