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
Letters in Organic Chemistry
Title: Enantioselective Synthesis of 2, 6-Disubstituted Dihydropyrone Derivatives Catalyzed by TiCl4/BINOL/RONa System
Volume: 5 Issue: 5
Author(s): Yuan-Cong Zhao, Ji Zhang, Na Wang, Hong Yu, Xin-Bing Yang, Shan-Yong Chen and Xiao-Qi Yu
Affiliation:
Keywords: HDA reaction, dihydropyrones, enantioselective synthesis, BINOL, Na alcoholate
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.
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Cite this article as:
Zhao Yuan-Cong, Zhang Ji, Wang Na, Yu Hong, Yang Xin-Bing, Chen Shan-Yong and Yu Xiao-Qi, Enantioselective Synthesis of 2, 6-Disubstituted Dihydropyrone Derivatives Catalyzed by TiCl4/BINOL/RONa System, Letters in Organic Chemistry 2008; 5 (5) . https://dx.doi.org/10.2174/157017808784872016
DOI https://dx.doi.org/10.2174/157017808784872016 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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