发明授权
- 专利标题: Optically active axially chiral alpha-allenic alcohol, synthesis method and use thereof
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申请号: US14401051申请日: 2012-11-20
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公开(公告)号: US09701601B2公开(公告)日: 2017-07-11
- 发明人: Shengming Ma , Juntao Ye
- 申请人: SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES
- 申请人地址: CN Shanghai
- 专利权人: SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES
- 当前专利权人: SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES
- 当前专利权人地址: CN Shanghai
- 代理机构: Birch, Stewart, Kolasch & Birch, LLP
- 优先权: CN201210193176 20120612
- 国际申请: PCT/CN2012/084896 WO 20121120
- 国际公布: WO2013/185435 WO 20131219
- 主分类号: C07C29/17
- IPC分类号: C07C29/17 ; C07C311/16 ; C07C33/03 ; C07C33/12 ; C07C67/343 ; C07C29/00 ; C07D307/30 ; C07D307/28 ; C07C33/14
摘要:
The present invention relates to an optically active axially chiral α-allenic alcohol, a synthesis method and use thereof. The invention relates to a method of preparing a highly optically active chiral α-allenic alcohol by using propargyl alcohol, aldehyde and chiral α,α-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with an accelerant zinc bromide. The axially chiral α-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high universality, the total yield is high, and enantioselectivity and diastereoselectivity are high. The highly optically active axially chiral α-allenic alcohol synthesized by the method of the present invention can conveniently synthesize 2,5-dihydrofuran compounds having central chirality and complete chirality, and at the same time can further synthesize axially chiral allenic amine and allenic malonic ester compounds having complete chirality.
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