Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form
As of April 1st VIVO Scientific Profiles will no longer updated for faculty, and the link to VIVO will be removed from the library website. Faculty profile pages will continue to be updated via Interfolio. VIVO will continue being used behind the scenes to update graduate student profiles. Please contact helplib@scripps.edu if you have questions.
How to download citations from VIVO | Alternative profile options

Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

authors

  • Kister, J.
  • Ess, D. H.
  • Roush, William

publication date

  • November 2013

journal

  • Organic Letters  Journal

abstract

  • An enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylate esters 3 via the reductive aldol reaction of ethyl allenecarboxylate (2) with 10-trimethylsilyl-9-borabicyclo[3.3.2]decane (1R) has been developed. Density functional theory calculations suggest that the allene hydroboration involves the 1,4-reduction of 2 with the 1R, leading directly to dienolborinate Z-(O)-8a.

subject areas

  • Bicyclo Compounds
  • Boron Compounds
  • Carboxylic Acids
  • Esters
  • Molecular Structure
  • Stereoisomerism
  • Trimethylsilyl Compounds
  • Vinyl Compounds
scroll to property group menus

Identity

PubMed Central ID

  • PMC3849616

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol4025277

PubMed ID

  • 24138187
scroll to property group menus

Additional Document Info

start page

  • 5436

end page

  • 5439

volume

  • 15

issue

  • 21

©2022 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support