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2005
Carbohydrates
U 0500
A Substrate Controlled, Very Highly Diastereoselective Morita—Baylis—Hillman
A Remote Activation of the Diastereofacial Selectivity in the Synthesis
14- 194 Reaction:
of C-3-Branched Deoxysugars. — A highly diastereoselective route towards synthetically valuable 4-substituted pyran-3-one derivatives is provided by Morita—Baylis—
Hillman reaction of C6 acyl protected enulosides (I) and aldehydes. The excellent
stereoselectivity observed in these reactions is explained based on a Zimmerman—Traxler-type transition state model. — (SAGAR, R.; PANT, C. S.; PATHAK, R.;
SHAW*, A. K.; Tetrahedron 60 (2004) 50, 11399-11406; Div. Med. Chem., Cent.
Drug Res. Inst., Lucknow 226 001, India; Eng.) — Nuesgen
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