Asymmetric synthesis of .alpha.-functionalized primary sulfonamides
作者:Franklin A. Davis、Ping Zhou、Patrick J. Carroll
DOI:10.1021/jo00070a026
日期:1993.8
Alpha-Functionalized primary sulfonamides 8 are prepared in good to excellent yields by treatment of the dianions of N-sulfonylcamphorimines 1-3 with electrophiles and hydrolysis of the resulting imines 5-7. Alkylation of the anions of N-sulfonyl-10-camphorsulfonamide imines 2 and 3 with primary and secondary alkyl iodides and with ethylene oxide, following removal of the chiral auxiliary with aqueous acid, gave primary sulfonamides with ee's in the range of 66-95%.
A new synthesis of α-functionalized unsubstituted sulfonamides