Development of a Nonenzymatic Kinetic Resolution of α-Allenic Alcohols

Yan Wang; Rob Hoen; Ran Hong

doi:10.1055/s-0032-1317566

Synlett, Table of Contents

Synlett 2012; 23(19): 2729-2734
DOI: 10.1055/s-0032-1317566

synpacts

Development of a Nonenzymatic Kinetic Resolution of α-Allenic Alcohols

Yan Wang

^aKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, P. R. of China Fax: +862164166128 Email: rhong@sioc.ac.cn

,

Rob Hoen

^bGP Pharm, Isaac Peral 17 Polígon Camí Ral, 08850 Gavà (Barcelona), Spain

,

Ran Hong*

^aKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, P. R. of China Fax: +862164166128 Email: rhong@sioc.ac.cn

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Abstract

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Abstract

This personal viewpoint lays out the development of a silver-catalyzed kinetic resolution of α-allenic alcohols inspired by the biomimetic synthesis of natural products. The corresponding selectivity factor (s) indicates that this resolution protocol can deliver chiral allenic alcohols and 2,5-dihydrofurans in high enantioselectivity with synthetically applicable isolated yields. The broad substrate scope makes it an attractive approach for building synthetically useful chiral building blocks. From the recent progress in allene chemistry, silver was considered as an anion metathesis reagent to prepare highly efficient Au catalysts. Our discovery of the unique reactivity of a chiral silver phosphate should stimulate more interesting discoveries in this field.

Key words

kinetic resolution - allenic alcohol - chiral silver phosphate - cycloisomerization - natural products

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References

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