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200517.fm Page 32 Friday, March 18, 2005 2:52 PM
2005
Enantioselective syntheses
O 0031
Dimethylsilyl Ketene Acetal as a Nucleophile in Asymmetric Michael Reaction:
Enantioselectivity in Oxazaborolidinone-Catalyzed Reaction. — The
17- 032 Enhanced
use of silyl ether (II) as a nucleophile in place of the conventional Tms-analogue,
enhances the enantioselectivity of the BPT-catalyzed asymmetric Michael reaction.
Furthermore, scope of the reaction with respect to the enone structure can be extended.
Enantioselectivities up to 98% e.e. are achieved for a variety of acyclic enones. —
(HARADA*, T.; ADACHI, S.; WANG, X.; Org. Lett. 6 (2004) 26, 4877-4879; Dep.
Chem. Mater. Technol., Kyoto Inst. Technol., Sakyo, Kyoto 606, Japan; Eng.) —
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