☆ 4.8 Article

Ruthenium-Catalyzed Asymmetric N-Demethylative Rearrangement of Isoxazolidines and Its Application in the Asymmetric Total Syntheses of (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12

ORGANIC LETTERS (2014)

Journal

ORGANIC LETTERS

Volume 16, Issue 24, Pages 6512-6514

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol503261h

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Categories

Chemistry, Organic

Funding

National Natural Science Foundation of China [NSFC 21404096]
Fundamental Research Funds for the Central Universities of China [WK2060190022, WK2060190026]
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Abstract

An asymmetric N-demethylative rearrangement of 1,2-isoxazolidines catalyzed by ruthenium is described. Enantioenriched syn-1,3-aminoalcohols as well as cis-1,3-oxazinanes, which are useful building blocks, can be efficiently prepared stereospecifically by this reaction in good yields, via the isoxazolidine intermediates in situ generated from a nitrone bearing a chiral auxiliary and styrenes. This asymmetric reaction was also applied in the asymmetric total syntheses of both (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12.

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