Preparation of chiral α-substituted alaninates through an efficient diastereoselective synthesis of trisubstituted allylic alcohols

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1 Citation (Scopus)

Abstract

Tri without fail: The highly diastereoselective addition of vinylaluminum reagents, generated in situ from the zirconium-catalyzed carboalumination of various alkynes and Me3Al, to the easily accessible (2S,5R,6R)-5,6-dimethyl-[1,4]dioxane-2-carbaldehyde (1 b) afforded the corresponding trisubstituted allylic alcohols, and a subsequent Overman reaction yielded allylic amines that contain chiral quaternary carbon stereocenters.

Original languageEnglish
Pages (from-to)80-83
Number of pages4
JournalChemistry - An Asian Journal
Volume8
Issue number1
DOIs
Publication statusPublished - 2013 Jan 1

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Alkynes
Amines
Carbon
dimethyldioxane
allyl alcohol

Keywords

  • allylic compounds
  • amines
  • butane-1,2-diacetal-protected L -glyceraldehyde
  • diastereoselectivity
  • α-substituted alaninates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

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title = "Preparation of chiral α-substituted alaninates through an efficient diastereoselective synthesis of trisubstituted allylic alcohols",
abstract = "Tri without fail: The highly diastereoselective addition of vinylaluminum reagents, generated in situ from the zirconium-catalyzed carboalumination of various alkynes and Me3Al, to the easily accessible (2S,5R,6R)-5,6-dimethyl-[1,4]dioxane-2-carbaldehyde (1 b) afforded the corresponding trisubstituted allylic alcohols, and a subsequent Overman reaction yielded allylic amines that contain chiral quaternary carbon stereocenters.",
keywords = "allylic compounds, amines, butane-1,2-diacetal-protected L -glyceraldehyde, diastereoselectivity, α-substituted alaninates",
author = "Balraj Gopula and Lee, {Way Zen} and Wu, {Hsyueh Liang}",
year = "2013",
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T1 - Preparation of chiral α-substituted alaninates through an efficient diastereoselective synthesis of trisubstituted allylic alcohols

AU - Gopula, Balraj

AU - Lee, Way Zen

AU - Wu, Hsyueh Liang

PY - 2013/1/1

Y1 - 2013/1/1

N2 - Tri without fail: The highly diastereoselective addition of vinylaluminum reagents, generated in situ from the zirconium-catalyzed carboalumination of various alkynes and Me3Al, to the easily accessible (2S,5R,6R)-5,6-dimethyl-[1,4]dioxane-2-carbaldehyde (1 b) afforded the corresponding trisubstituted allylic alcohols, and a subsequent Overman reaction yielded allylic amines that contain chiral quaternary carbon stereocenters.

AB - Tri without fail: The highly diastereoselective addition of vinylaluminum reagents, generated in situ from the zirconium-catalyzed carboalumination of various alkynes and Me3Al, to the easily accessible (2S,5R,6R)-5,6-dimethyl-[1,4]dioxane-2-carbaldehyde (1 b) afforded the corresponding trisubstituted allylic alcohols, and a subsequent Overman reaction yielded allylic amines that contain chiral quaternary carbon stereocenters.

KW - allylic compounds

KW - amines

KW - butane-1,2-diacetal-protected L -glyceraldehyde

KW - diastereoselectivity

KW - α-substituted alaninates

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