Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6787-6790

  Majewski, Marek ^a   Shao, Jianxing ^a   Nelson, Ken ^a   Nowak, Pawel ^a   Irvine, Nicholas M ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Alkaloids; Enantioselective deprotonation; Indolizidines

Indexed keywords

1 DEOXYCASTANOSPERMINE; 1 HYDROXYINDOLIZIDINE DERIVATIVE; INDOLIZIDINE DERIVATIVE; N BUTYLOXYCARBONYLPYRROLIDINE; PYRROLIDINE DERIVATIVE; SPARTEINE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032541723     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01491-9     Document Type: Article

References (28)

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26. 6: C, 65.56; H, 8.31; N, 3.33. Found: C, 65.63; H, 8.42; N, 3.01.
27. 1H-NMR: 4.19 (dd, J=6.1, 8.0, 1H), 3.73-3.67 (m, 2H), 3.24 (dd, J=7.5, 6.2, 1H), 3.05-2.92 (m, 2H), 2.80-2.69 (m, 2H), 1.97-1.74 (m, 5H) 1.45 (s, 6H).
28. 10. Apparently some structural assignments in reference 3h were incorrect. Structure labelled 21aa on page 3081 in this reference should be 21ba (and vice versa) and structure 21bb should be exchanged with 21ab. We thank Professor Chan for this information and for the copies of relevant spectra (see also ref. 3b, footnote 6).