Practical one-pot sequence for the asymmetric synthesis of 1,2 diols from primary alcohols

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• 作者：Philippe Hermange ; Franç ; ois Portalier ; Christine Thomassigny ; Christine Greck ; ^{greck@chimie.uvsq.fr}
• 关键词：1 ; 2-Diol ; TEMPO ; Asymmetric benzoyloxylation ; Electrophilic hydroxylation ; Organocatalysis ; One-pot sequence
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：27 February, 2013
• 年：2013
• 卷：54
• 期：9
• 页码：1052-1055
• 全文大小：1763 K

文摘

A practical one-pot three-step sequence is reported for the asymmetric synthesis of ¦Á-benzoyloxylated alcohols from primary alcohols. Good overall yields (36-52 % ) and enantioselectivities (91-94 % e.e.) are obtained using a commercial organocatalyst in the key oxylation reaction. A simple modification in the protocol allows the formation of enantioenriched ¦Ã-benzoyloxylated ¦Á,¦Â-unsaturated ester from alcohol. Synthetic utility has been harnessed to the easy preparation of (?)-¦Ã-octalactone from hexan-1-ol.