Influence of alpha-methyl substitution of proline-based organocatalysts on the asymmetric alpha-oxidation of aldehydes

Tong, Sok; Brimble, Margaret; Barker, David

dc.contributor.author	Tong, Sok	en
dc.contributor.author	Brimble, Margaret	en
dc.contributor.author	Barker, David	en
dc.date.accessioned	2011-10-25T01:55:50Z	en
dc.date.issued	2009	en
dc.identifier.citation	Tetrahedron 65(25):4801-4807 2009	en
dc.identifier.issn	0040-4020	en
dc.identifier.uri	http://hdl.handle.net/2292/8424	en
dc.description.abstract	The direct asymmetric organocatalytic a-oxidation of aldehydes using trans-2-(p-methylphenylsulfonyl)-3-phenyloxaziridine is reported. This method affords the S isomer of alpha-hydroxy aldehydes, thereby complementing the selectivity for the R isomer observed using the two-step nitrosobenzene method. Use of alpha-methylproline and alpha-methylproline tetrazole significantly increases the enantioselectivity observedfor the alpha-oxidation of aldehydes compared to analogous unsubstituted organocatalysts.	en
dc.language	EN	en
dc.publisher	Elsevier Ltd.	en
dc.relation.ispartofseries	Tetrahedron	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/0040-4020/	en
dc.rights.uri	https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm	en
dc.subject	SILYL ENOL ETHERS	en
dc.subject	3-COMPONENT MANNICH REACTION	en
dc.subject	METALATED CHIRAL HYDRAZONES	en
dc.subject	AMINO-ACID-DERIVATIVES	en
dc.subject	ENANTIOSELECTIVE SYNTHESIS	en
dc.subject	N-SULFONYLOXAZIRIDINES	en
dc.subject	1,2-AMINO ALCOHOLS	en
dc.subject	HYDROXY ALDEHYDES	en
dc.subject	CARBONYL-COMPOUNDS	en
dc.subject	MOLECULAR-OXYGEN	en
dc.title	Influence of alpha-methyl substitution of proline-based organocatalysts on the asymmetric alpha-oxidation of aldehydes	en
dc.type	Journal Article	en
dc.identifier.doi	10.1016/j.tet.2009.04.060	en
pubs.issue	25	en
pubs.begin-page	4801	en
pubs.volume	65	en
dc.rights.holder	Copyright: PERGAMON-ELSEVIER SCIENCE LTD	en
pubs.end-page	4807	en
dc.rights.accessrights	http://purl.org/eprint/accessRights/RestrictedAccess	en
pubs.subtype	Article	en
pubs.elements-id	85789	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