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

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

2 Scopus citations

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
State	Published - Jan 2013
Externally published	Yes

Keywords

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

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10.1002/asia.201200859

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

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",

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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

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 - α-substituted alaninates

KW - allylic compounds

KW - amines

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

KW - diastereoselectivity

UR - https://www.scopus.com/pages/publications/84871577866

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

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