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(Z)-α-Boryl-crotylboron reagents via Z-selective alkene isomerization and application to stereoselective syntheses of (E)-δ-boryl-syn-homoallylic alcohols† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc00226j
- Source :
- Chemical Science
- Publication Year :
- 2019
- Publisher :
- Royal Society of Chemistry, 2019.
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Abstract
- Stereoselective synthesis of (Z)-α-boryl-crotylboronate is developed.<br />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.
- Subjects :
- Chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 20416539 and 20416520
- Volume :
- 10
- Issue :
- 12
- Database :
- OpenAIRE
- Journal :
- Chemical Science
- Accession number :
- edsair.pmc...........330751ee0d5ff13a27dc21aa02f1286e