Chromium(II) chloride-mediated coupling reactions of Garner aldehyde with allyl bromides: facile asymmetric synthesis of (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine

Authors
Aoyagi, Y Inaba, H Hiraiwa, Y Kuroda, A Ohta, A
Citation
Y. Aoyagi et al., Chromium(II) chloride-mediated coupling reactions of Garner aldehyde with allyl bromides: facile asymmetric synthesis of (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine, J CHEM S P1, (23), 1998, pp. 3975-3978
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
23
Year of publication
1998
Pages
3975 - 3978
Database
ISI
SICI code
0300-922X(199812):23<3975:CCCROG>2.0.ZU;2-K
Abstract
Chromium(II) chloride-mediated coupling reactions of 1,1-dimethylethyl (S)- and (R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylates [(S)- and (R)-Garn er aldehydes] (1a,b) with allyl bromides 2a-c proceeded with moderate to go od stereoselectivity to give the corresponding homoallyl alcohols 3a-d in g ood yields. The homoallyl alcohol 3b was easily transformed to (2R,3S)-3-hy droxy-2-hydroxymethylpyrrolidine 8.