Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 39, Pages 14524-14527Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4072145
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Funding
- NSF [CHE-0957462]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0957462] Funding Source: National Science Foundation
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We report absolute and relative stereo chemistry of addition in enantioselective chlorolactonizations of 4-phenyl-4-pentenoic acid and its related t-butyl ester, catalyzed by (DHQD)(2)PHAL. Predominant syn addition of the chlorenium and the nudeophile across the olefin is observed. As shown by isotopic labeling, NMR spectroscopy, and derivative studies, the two new stereo-centers formed by addition across the double bond are set independently and influenced by different factors. These findings suggest a stepwise process via an intermediate capable of lactone closure with either stereochemistry, in contradistinction to the more familiar scenario in which anti addition is dictated by a bridging chloronium ion intermediate.
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