Chiral alpha,beta-dialkoxy- and alpha-alkoxy-beta-aminostannanes: preparation and copper-mediated cross-coupling.
Addition of Zn(n-Bu(3)Sn)(2) to prochiral aldehydes affords anti-alpha,beta-dialkoxy- and anti-alpha-alkoxy-beta-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de). syn-Isomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(I)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration. [reaction: see text]
Mohapatra
Suchismita
S
Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA.
Bandyopadhyay
A
A
Barma
D K
DK
Capdevila
Jorge H
JH
Falck
J R
JR
D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009947:Organotin Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D009947:Organotin Compounds; D003300:Copper