Asymmetric allylation of sulfonyl imines catalyzed by in situ generated Cu(II) complexes of chiral amino alcohol based Schiff bases

作者:Ghosh Debashis; Bera Prasanta Kumar; Kumar Manish; Abdi Sayed H R*; Khan Noor ul H; Kureshy Rukhsana I; Bajaj Hari C
来源:RSC Advances, 2014, 4(99): 56424-56433.
DOI:10.1039/c4ra10929e

摘要

A catalytic route for enantioselective synthesis of homoallyl amines through Cu(II)-Schiff base catalyzed reaction of allyltin with aryl, alkenyl-substituted N-sulfonylimines is described. The allylation reaction is promoted by a simple in situ generated Cu(II)-amino alcohol based Schiff base complex. The addition of allyltin to aldimines delivers the desired products up to 90% yield and 98% enantiomeric excess (ee). Based on experimental observations a probable mechanism was proposed for this reaction. The current methodology was extended to the synthesis of beta-phenylalanine in good yield and very good enantioselectivity.

  • 出版日期2014
  • 单位海洋化工研究院有限公司