Journal
ORGANIC LETTERS
Volume 13, Issue 15, Pages 3868-3871Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2013999
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Funding
- National Natural Science Foundation of China [20732003, 21021001, 20902060]
- Basic Research Program of China [2010CB833300]
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A highly diastereo- and enantioselective hetero-Diels-Alder (HDA) reaction of a Brassard-type diene with aliphatic aldehydes has been developed. The chiral N,N'-dioxide L2/In(OTf)(3) complex was efficient toward the obtention of the corresponding beta-methoxy-gamma-methyl alpha,beta- unsaturated delta-lactones in good yields (up to 86%) as well as dr and ee values (up to 97:3 cis/trans and 94% ee). In addition, the product 4a could be easily transformed into the methyl-protected epi-prelactone B by hydrogenation.
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