Enantioselective synthesis of alpha-halo-alpha-alkylmalonates via phase-transfer catalytic alpha-alkylation

  • Hong, Suckchang
  • Kim, Minsik
  • Jung, Myunggi
  • Ha, Min Woo
  • Lee, Myungmo
  • ... Kim, Mi-hyun
  • 외 4명
Citations

WEB OF SCIENCE

10
Citations

SCOPUS

10

초록

A new enantioselective synthetic method for alpha-halo-alpha-alkylmalonates is reported. alpha-Alkylation of diphenylmethyl tert-butyl alpha-halomalonates under phase-transfer catalytic conditions (solid KOH, toluene, -40 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide (5 mol%) afforded diphenylmethyl tert-butyl alpha-halo-alpha-alkylmalonates in very high chemical yields (up to 99%) and optical yields (up to 93% ee).

키워드

QUATERNARY STEREOGENIC CENTERS1,3-DICARBONYL COMPOUNDSCONJUGATE ADDITIONMICHAEL REACTIONBUILDING-BLOCKSAMINO-ACIDSESTERSCONSTRUCTIONNITROALKENESFLUORINATION
제목
Enantioselective synthesis of alpha-halo-alpha-alkylmalonates via phase-transfer catalytic alpha-alkylation
저자
Hong, SuckchangKim, MinsikJung, MyunggiHa, Min WooLee, MyungmoPark, YohanKim, Mi-hyunKim, Taek-SooLee, JihoonPark, Hyeung-geun
DOI
10.1039/c3ob42107d
발행일
2014-03
유형
Article
저널명
Organic and Biomolecular Chemistry
12
9
페이지
1510 ~ 1517