Synthesis of enantioenriched α-(hydroxyalkyl)-tri-n-butylstannanes

Anyu He, J R Falck

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

(Chemical Equation Presented) Li and Mg are pesky: A catalytic asymmetric synthesis of α-(hydroxyalkyl)-tri-n-butylstannanes (1) in good to excellent yields and enantioselectivities was achieved (see scheme; PG=protecting group; L*=chiral ligand). Compound 1 was isolated as an ester or thiocarbamate, and the reagent was prepared from equimolar amounts of nBu3SnH and Et2Zn in dimethoxyethane. Conditions employing lithium or magnesium ions suppress enantioselectivity.

Original languageEnglish (US)
Pages (from-to)6586-6589
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number35
DOIs
StatePublished - Aug 18 2008

Fingerprint

Thiocarbamates
Enantioselectivity
Lithium
Magnesium
Esters
Ions
Ligands
1,2-dimethoxyethane

Keywords

  • Aldehydes
  • Asymmetric synthesis
  • Organometallic compounds
  • Tin
  • Zinc

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

Cite this

Synthesis of enantioenriched α-(hydroxyalkyl)-tri-n-butylstannanes. / He, Anyu; Falck, J R.

In: Angewandte Chemie - International Edition, Vol. 47, No. 35, 18.08.2008, p. 6586-6589.

Research output: Contribution to journalArticle

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