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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Enantioselective Synthesis of 2, 6-Disubstituted Dihydropyrone Derivatives Catalyzed by TiCl4/BINOL/RONa System

Author(s): Yuan-Cong Zhao, Ji Zhang, Na Wang, Hong Yu, Xin-Bing Yang, Shan-Yong Chen and Xiao-Qi Yu

Volume 5, Issue 5, 2008

Page: [391 - 395] Pages: 5

DOI: 10.2174/157017808784872016

Price: $65

Abstract

A facile method for the preparation of chiral pyrone derivatives through hetero-Diels-Alder reaction is described. Sodium alcoholates were used as efficient additives in the enantioselective reactions catalyzed by MCl4 (M = Ti4+, Sn4+) / (R)-BINOL systems. The optically resulted active 2, 6-disubsituted dihydropyrones could be obtained with up to 94% ees and 88% yields.

Keywords: HDA reaction, dihydropyrones, enantioselective synthesis, BINOL, Na alcoholate


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