Stereoselective radical addition of an acetal to sterically tuned enantiomerically pure N-sulfinyl imines.
Enantiomerically enriched sulfonamides were synthesized by the radical addition of an acetal to enantiomerically pure N-sulfinyl imines using dimethylzinc-air and boron trifluoride diethyl etherate. Higher levels of stereocontrol were observed by using a mesitylenesulfinyl group. Furthermore, an amine and an amino alcohol with high enantiomeric purity were obtainable from the sulfonamide product.
Akindele
Tito
T
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Yamada
Ken-ichi
K
Sejima
Takumi
T
Maekawa
Masaru
M
Yamamoto
Yasutomo
Y
Nakano
Mayu
M
Tomioka
Kiyoshi
K
D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
D000080:Acetals; D001880:Boranes; D007097:Imines; D009942:Organometallic Compounds; D013449:Sulfonamides; C101707:boron trifluoride etherate; C511262:dimethylzinc