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Synthesis of homochiral spiro [4.4]nonane‐l,6‐diols
Author(s) -
YaoZhong Jiang,
Minga Yan,
Jian Sun,
WenHao Hu,
Zhi Li,
AiQiao Mi,
Albert S. C. Chan
Publication year - 1998
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19980160310
Subject(s) - chemistry , nonane , diol , yield (engineering) , lithium (medication) , hydride , lithium aluminium hydride , cis–trans isomerism , stereochemistry , medicinal chemistry , organic chemistry , metal , medicine , materials science , metallurgy , endocrinology
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.