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Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol

Academic Article
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Overview

related to degree

  • Chen, Ming, Ph.D. in Organic Chemistry, Scripps Research 2007 - 2012

authors

  • Chen, Ming
  • Roush, William

publication date

  • June 2010

journal

  • Organic Letters  Journal

abstract

  • Delta-methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF(3).Et(2)O-promoted allylboration with alpha-Me-allylboronate 1. The origin of high (E)-selectivity is proposed.

subject areas

  • Alcohols
  • Aldehydes
  • Allyl Compounds
  • Boronic Acids
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2891445

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol1007444

PubMed ID

  • 20476769
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Additional Document Info

start page

  • 2706

end page

  • 2709

volume

  • 12

issue

  • 12

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