(Z)-α-Boryl-crotylboron reagents via Z-selective alkene isomerization and application to stereoselective syntheses of (E)-δ-boryl-syn-homoallylic alcohols?
Chemical Science Pub Date: 2019-02-26 DOI: 10.1039/C9SC00226J
Abstract
Stereoselective synthesis of (Z)-α-boryl-crotylboronate is developed. Ni-catalyzed Z-selective alkene isomerization of α-boryl substituted homoallylboronate provided the targeted (Z)-crotylboronate with high selectivity. Stereoselective addition of the novel crotylboron reagent to aldehydes gave (E)-δ-boryl-substituted syn-homoallylic alcohols with excellent diastereoselectivities. The vinyl boronate unit in the products can be directly used for a subsequent C–C bond-forming transformation as illustrated in the synthesis of the C1–7 fragment of the natural products nannocystin A and nannocystin Ax.
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Journal Name：Chemical Science
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CAS no.: 89640-58-4
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