Journal article icon

Journal article

Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (-)-codonopsinine

Abstract:

Ring-closing iodoamination of (E)-configured, N-α-methyl-p- methoxybenzyl protected homoallylic amines upon treatment with I 2 and NaHCO 3 in MeCN occurs with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl croto...

Expand abstract
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1016/j.tet.2012.03.045

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Roberts, PM More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
TETRAHEDRON
Volume:
68
Issue:
22
Pages:
4302-4319
Publication date:
2012-06-03
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
URN:
uuid:004ccd06-3877-4dfa-ad98-1234a43fe88e
Source identifiers:
331933
Local pid:
pubs:331933

Terms of use


Metrics



If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP