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(Z)-?-Boryl-crotylboron reagents via Z-selective alkene isomerization and application to stereoselective syntheses of (E)-?-boryl-syn-homoallylic alcohols.


ABSTRACT: Stereoselective synthesis of (Z)-?-boryl-crotylboronate is developed. Ni-catalyzed Z-selective alkene isomerization of ?-boryl substituted homoallylboronate provided the targeted (Z)-crotylboronate with high selectivity. Stereoselective addition of the novel crotylboron reagent to aldehydes gave (E)-?-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.

SUBMITTER: Gao S 

PROVIDER: S-EPMC6432281 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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(<i>Z</i>)-α-Boryl-crotylboron reagents <i>via Z</i>-selective alkene isomerization and application to stereoselective syntheses of (<i>E</i>)-δ-boryl-<i>syn</i>-homoallylic alcohols.

Gao Shang S   Chen Jichao J   Chen Ming M  

Chemical science 20190226 12


Stereoselective synthesis of (<i>Z</i>)-α-boryl-crotylboronate is developed. Ni-catalyzed <i>Z</i>-selective alkene isomerization of α-boryl substituted homoallylboronate provided the targeted (<i>Z</i>)-crotylboronate with high selectivity. Stereoselective addition of the novel crotylboron reagent to aldehydes gave (<i>E</i>)-δ-boryl-substituted <i>syn</i>-homoallylic alcohols with excellent diastereoselectivities. The vinyl boronate unit in the products can be directly used for a subsequent C-  ...[more]

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