Chirality transfer from a biphenyl axis to a spiro centre and its reverse:sequential self-immolation

Authors
Baker, RW Kyasnoor, RV Sargent, MV
Citation
Rw. Baker et al., Chirality transfer from a biphenyl axis to a spiro centre and its reverse:sequential self-immolation, TETRAHEDR L, 40(17), 1999, pp. 3475-3478
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
17
Year of publication
1999
Pages
3475 - 3478
Database
ISI
SICI code
0040-4039(19990423)40:17<3475:CTFABA>2.0.ZU;2-H
Abstract
Schmidt reaction of (S)-1-(2,'4',6-trimethoxy-4,6'-dimethylbiphenyl-2-yl)et hanone 8 furnished the expected amide 9 (43%) accompanied by (S)-2,7'-dimet hoxy-3',5',6-trimethylspiro[cyclohexa-2,5-diene-1,1'-(1H)isoindole]-4-one 1 2 (30%) which on reduction with zinc and acetic acid and subsequent methyla tion regenerated ketone 8. (C) 1999 Elsevier Science Ltd. All rights reserv ed.