dc.contributor.author |
Brimble, Margaret |
en |
dc.contributor.author |
Lee, CY |
en |
dc.date.accessioned |
2011-09-19T01:54:10Z |
en |
dc.date.issued |
1998 |
en |
dc.identifier.citation |
Tetrahedron: Asymmetry 9(5), 873-884,1998 |
en |
dc.identifier.issn |
0957-4166 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8075 |
en |
dc.description.abstract |
The preparation of di-(−)-(1R,2S)-2-phenyl-1-cyclohexyl diazenedicarboxylate 4 is described. Reaction of (1R,2S)-2-phenyl-1-cyclohexanol 1 with excess phosgene in the presence of quinoline afforded chloroformate 2 which was treated directly with hydrazine monohydrate (0.5 equiv.) to afford di-(−)-(1R,2S)-2-phenyl-1-cyclohexyl diazanedicarboxylate 3. Oxidization of 3 to the azo-enophile 4 was then readily effected in high yield using N-bromosuccinimide and pyridine. The azo-ene reactions of 4 with the alkenes cyclohexene 5, cyclopentene 6, trans-3-hexene 7 and trans-4-octene 8 were carried out using the Lewis acid tin(IV) chloride. Use of cyclohexene 5 afforded the ene adduct 9 in 80% yield with a diastereomeric excess of >97:3 whilst the use of cyclopentene 6, trans-3-hexene 7 and trans-4-octene 8 afforded the ene adducts 10 (77%), 11 (71%) and 12 (92%) with a diastereomeric excess of 86:14 in each case. Use of the conjugated aromatic acyclic alkene 13 afforded the product of an ionic addition, namely, chloride 14 in 57% yield. Cleavage of the N–N bond of the ene adduct 9 was effected using lithium in liquid ammonia affording the carbamate 16 in moderate yield. |
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dc.language |
EN |
en |
dc.relation.ispartofseries |
Tetrahedron-Asymmetry |
en |
dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0957-4166/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
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dc.subject |
ELECTROPHILIC AMINATION REACTIONS |
en |
dc.subject |
ALLYLIC AMINATION |
en |
dc.subject |
ORGANIC-SYNTHESIS |
en |
dc.subject |
ACHIRAL ESTER |
en |
dc.subject |
AZODICARBOXYLATE |
en |
dc.subject |
DIAZANEDICARBOXYLATE |
en |
dc.subject |
INDUCTION |
en |
dc.subject |
OXIDATION |
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dc.subject |
ALKENES |
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dc.title |
Asymmetric Azo-ene Reactions Using the Chiral Azo-enophile Di-(-)-(1R,2S)-2-phenyl-1-cyclohexyl Diazenedicarboxylate |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1016/S0957-4166(98)00034-2 |
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pubs.issue |
5 |
en |
pubs.begin-page |
873 |
en |
pubs.volume |
9 |
en |
dc.rights.holder |
Copyright: 1998 Elsevier Science Ltd. |
en |
pubs.end-page |
884 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
33973 |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
pubs.org-id |
Science Research |
en |
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
en |
pubs.record-created-at-source-date |
2010-09-01 |
en |