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Synthesis of homochiral spiro [4.4]nonane-l,6-diols

✍ Scribed by Jiang Yao-Zhong; Yan Minga; Sun Jian; Hu Wen-Hao; Li Zhi; Mi Ai-Qiao; Chan Albert S. C.

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 332 KB
Volume: 16
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.19980160310

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✦ Synopsis

Abstract

Homochiral cis, cis‐; cis,trans and trans,trans‐spiro[4,4]‐nonane‐1,6‐diols were prepared via diastereoselective reduction of enantiomerically pure spiro[4.4]nonane‐l,6‐dione (1) with the corresponding reducing agents: lithium n‐butyldiisobutylaluminium hydride for cis,cis‐diol (2) with 88% yield; BH~3~·THF for cis, trans‐diol (8) with 91% yield; LiAlH~4~ for trans,trans‐diol (4) with 15% yield.

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