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Org Lett. 2009 Oct 15;11(20):4628-31. doi: 10.1021/ol901902v.

Unexpected regioselectivity in the synthesis of pyranonaphthoquinone via the Diels-Alder reaction.

Author information

1
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871, China.

Abstract

The unusual regioselectivity in the Diels-Alder reactions of pyranoquinone 1 with (4,4-dimethoxybuta-1,3-dien-2-yloxy)trimethylsilane 2 are explored by both computations and experiments. The regioselectivity is controlled by the electrostatic interaction of the lactone ring-oxygen and the vicinal quinone oxygen on the transition structure, which can be tuned by the terminal methyl group of the butadienes.

PMID:
19757828
DOI:
10.1021/ol901902v
[Indexed for MEDLINE]

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