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

Balraj Gopula; Way Zen Lee; Hsyueh Liang Wu

doi:10.1002/asia.201200859

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

Balraj Gopula, Way Zen Lee, Hsyueh Liang Wu^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (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 language	English
Pages (from-to)	80-83
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	8
Issue number	1
DOIs	https://doi.org/10.1002/asia.201200859
Publication status	Published - 2013 Jan

Keywords

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

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

Access to Document

10.1002/asia.201200859

Cite this

@article{9ae61ab7e8af4afcbcdc5c119c5446b8,

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",

month = jan,

doi = "10.1002/asia.201200859",

language = "English",

volume = "8",

pages = "80--83",

journal = "Chemistry - An Asian Journal",

issn = "1861-4728",

publisher = "John Wiley and Sons Ltd",

number = "1",

}

TY - JOUR

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

Y1 - 2013/1

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

UR - http://www.scopus.com/inward/record.url?scp=84871577866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84871577866&partnerID=8YFLogxK

U2 - 10.1002/asia.201200859

DO - 10.1002/asia.201200859

M3 - Article

AN - SCOPUS:84871577866

SN - 1861-4728

VL - 8

SP - 80

EP - 83

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 1

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this