Catalytic, Asymmetrictrans-Selective Hetero Diels−Alder Reactions Using a Chiral Zirconium Complex
- 15 March 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (7) , 1221-1223
- https://doi.org/10.1021/ol025745j
Abstract
The first catalytic, asymmetric 2,3-trans-selective hetero Diels−Alder reaction has been developed. The reactions of aldehydes with Danishefsky's dienes proceeded smoothly to afford the pyranone derivatives in high yields with high trans-selectivities and enantioselectivities in the presence of a chiral zirconium complex, which was prepared from zirconium tert-butoxide and (R)-3,3‘-diiodobinaphthol or its derivatives, primary alcohol, and a small amount of water. This reaction was applied to the concise synthesis of (+)-prelactone C.Keywords
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