Journal article

Inverted regioselectivity of C-H amination: Unexpected oxidation at beta- rather than gamma-C-H.

Abstract:: A rare example of beta- over gamma-C-H selectivity during Rh-catalysed sulfamate ester cyclisation is presented; from derivatives of 1,6-anhydro-beta-d-mannopyranose, five-membered sulfamidates were formed in preference to the typical six-membered oxathiazinane intramolecular insertion products. A 3D structure of sulfamate 1 helps to rationalise this unusual selectivity and analyses suggest that n-->sigma*(CH) interactions may be a key controlling factor.

Publication status:: Published

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APA Style

Wyszynski, F., Thompson, A., & Davis, B. (2010). Inverted regioselectivity of C-H amination: Unexpected oxidation at beta- rather than gamma-C-H. Organic and Biomolecular Chemistry, 8(19), 4246–4248.

MLA Style

Wyszynski, F, et al. “Inverted Regioselectivity of C-H Amination: Unexpected Oxidation at Beta- Rather than Gamma-C-H.” Organic and Biomolecular Chemistry, vol. 8, no. 19, 2010, pp. 4246–48.

Chicago Style

Wyszynski, F, A Thompson, and B Davis. 2010. “Inverted Regioselectivity of C-H Amination: Unexpected Oxidation at Beta- Rather than Gamma-C-H.” Organic and Biomolecular Chemistry 8 (19): 4246–48.
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Publisher copy:: 10.1039/c0ob00113a

Authors

+ Wyszynski, F More by this author

Role:: Author

+ Thompson, A More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Inorganic Chemistry
Role:: Author

+ Davis, B More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

Journal:: Organic and biomolecular chemistry More from this journal
Volume:: 8
Issue:: 19
Pages:: 4246-4248
Publication date:: 2010-10-01
DOI:: 10.1039/c0ob00113a
EISSN:: 1477-0539
ISSN:: 1477-0520

Language:: English
Pubs id:: pubs:66100
UUID:: uuid:04aa2d1d-d2d8-46d0-bc78-615f3f451a18
Local pid:: pubs:66100
Source identifiers:: 66100
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_04aa2d1dd2d846d0bc78615f3f451a18

Terms of use

Copyright date:: 2010

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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