Optically active axially chiral alpha-allenic alcohol, synthesis method and use thereof
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United States of America Patent
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Jul 11, 2017
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Nov 20, 2012
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Jun 12, 2012
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Abstract
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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