著者

安孫子 淳

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.54, no.7, pp.564-573, 1996-07-01 (Released:2010-01-28)

参考文献数

28

被引用文献数

2 3

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New chiral auxiliaries based on the isoxazolidine skeleton have been developed. Characteristic feature of these auxiliaries are : 1) High reactivity for asymmetric alkylations. 2) Acylation of the auxiliary with an acid chloride and an amine, or DCC condensation. 3) One step transformation of the reaction products to the corresponding chiral alcohols, aldehydes and ketones without loss of the stereochemical integrity with the recovery of the auxiliary. Asymmetric alkylation of chiral β-substituted alkanols via their triflates lead to the easy access to the “reduced polypropionate units” as well as the first synthesis of the marine natural product (+) -siphonarienone. Enantiomerically pure axially dissymmetric cyclohexylidene compounds were synthesized using asymmetric Horner-Emmons reaction of the phosphonate derived from the auxilliary.