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
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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 -