Journal article

Studies on the role of conformation and of hydrogen-bonding on the dihydroxylation of cyclic allylic alcohols: Application to the synthesis of conduritol D

Abstract:: A study on the dihydroxylation of a series of conformationally 'locked' cyclohexenols is reported. The orientation of the hydroxy group (i.e. equatorial or axial) is crucial in determining the degree of diastereoselectivity observed during oxidation. In some cases, the use of hydrogen-bonding enables the stereoselective synthesis of syn triols and tetraols. This effect has been utilised in the synthesis of conduritol D: X-ray crystal structure analysis provided a method of assigning the relative and absolute stereochemistry of an advanced synthetic intermediate.

Publication status:: Published

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APA Style

Donohoe, T., Moore, P., & Beddoes, R. (1997). Studies on the role of conformation and of hydrogen-bonding on the dihydroxylation of cyclic allylic alcohols: Application to the synthesis of conduritol D. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1, 43–51.

MLA Style

Donohoe, T, et al. “Studies on the Role of Conformation and of Hydrogen-Bonding on the Dihydroxylation of Cyclic Allylic Alcohols: Application to the Synthesis of Conduritol D.” JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, no. 1, 1997, pp. 43–51.

Chicago Style

Donohoe, T, P Moore, and R Beddoes. 1997. “Studies on the Role of Conformation and of Hydrogen-Bonding on the Dihydroxylation of Cyclic Allylic Alcohols: Application to the Synthesis of Conduritol D.” JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, no. 1: 43–51.
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Publisher copy:: 10.1039/a604052g

Authors

+ Donohoe, T More by this author

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

+ Moore, P More by this author

Role:: Author

+ Beddoes, R More by this author

Role:: Author

Journal:: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 More from this journal
Issue:: 1
Pages:: 43-51
Publication date:: 1997-01-07
DOI:: 10.1039/a604052g
EISSN:: 1364-5463
ISSN:: 0300-922X

Language:: English
Pubs id:: pubs:45483
UUID:: uuid:017f5f22-55b6-436a-92a0-20e2716aeaf5
Local pid:: pubs:45483
Source identifiers:: 45483
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_017f5f2255b6436a92a020e2716aeaf5

Terms of use

Copyright date:: 1997

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

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