External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan

Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the a-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetr...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 32; pp. 6121 - 6125
Main Authors Tomooka, K, Wang, LF, Okazaki, F, Nakai, T
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 05.08.2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
phthalan
bis(oxazoline)
ASYMMETRIC LITHIATION
isochroman
lithiation
BULI/CHIRAL BIS(OXAZOLINE) COMPLEX
enantioselection
Online AccessGet full text

Cover

More Information
Summary:Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the a-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)01028-5