A NOVEL BF(3)CENTER-DOT-OET(2)-CATALYZED [3-CBZ-ALPHA-AMINO ALDEHYDESWITH ALLYLTRIMETHYLSILANE - HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-2,3,5-TRISUBSTITUTED PYRROLIDINES(2] ANNULATION OF N)

Authors
KIYOOKA S SHIOMI Y KIRA H KANEKO Y TANIMORI S
Citation
S. Kiyooka et al., A NOVEL BF(3)CENTER-DOT-OET(2)-CATALYZED [3-CBZ-ALPHA-AMINO ALDEHYDESWITH ALLYLTRIMETHYLSILANE - HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-2,3,5-TRISUBSTITUTED PYRROLIDINES(2] ANNULATION OF N), Journal of organic chemistry, 59(8), 1994, pp. 1958-1960
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
8
Year of publication
1994
Pages
1958 - 1960
Database
ISI
SICI code
0022-3263(1994)59:8<1958:ANB[A>2.0.ZU;2-S
Abstract
In the presence of BF3.OEt(2) (0.2 molar equiv), the reactions (-10 de grees C, CH2Cl2) of N-Cbz-alpha-amino aldehydes with allyltrimethylsil ane produced pyrrolidines in good yields (70-80%), with high all-cis s tereoselectivity at the C12, C-3, and C-5 positions, along with small amounts of the expected homoallylic alcohols.