Journal article

Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives.

Abstract:: The camphor-derived tetrahydropyran (camTHP*)-desymmetrized glycinamide 1 undergoes efficient and highly diastereoselective lithium enolate Michael additions to nitro olefins, alpha,beta-unsaturated ketones, esters, and lactones. Straightforward manipulation of these products affords 3-substituted pyroglutamides and beta-aryl-alpha,gamma-diamino acid derivatives, highlighting the ease of synthesis of enantiomerically enriched, functionally dense molecules using this novel building block. [reaction: see text]

Publication status:: Published

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APA Style

Dixon, D., Horan, R., Monck, N., & Berg, P. (2004). Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives. Organic Letters, 6(24), 4427–4429.

MLA Style

Dixon, D, et al. “Highly Stereoselective Michael Addition Reactions of CamTHP*-Desymmetrized Glycinamide for the Synthesis of Functionally Dense Amino Acid Derivatives.” Organic Letters, vol. 6, no. 24, 2004, pp. 4427–29.

Chicago Style

Dixon, D, R Horan, N Monck, and P Berg. 2004. “Highly Stereoselective Michael Addition Reactions of CamTHP*-Desymmetrized Glycinamide for the Synthesis of Functionally Dense Amino Acid Derivatives.” Organic Letters 6 (24): 4427–29.
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Publisher copy:: 10.1021/ol048568q

Authors

+ Dixon, D More by this author

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

+ Horan, R More by this author

Role:: Author

+ Monck, N More by this author

Role:: Author

+ Berg, P More by this author

Role:: Author

Journal:: Organic letters More from this journal
Volume:: 6
Issue:: 24
Pages:: 4427-4429
Publication date:: 2004-11-01
DOI:: 10.1021/ol048568q
EISSN:: 1523-7052
ISSN:: 1523-7060

Language:: English
Keywords:: Glycine

Amino Acids

Camphor

Stereoisomerism
Pubs id:: pubs:39312
UUID:: uuid:0344eacd-4c8f-4ab0-b31a-dcafbfd147b6
Local pid:: pubs:39312
Source identifiers:: 39312
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_0344eacd4c8f4ab0b31adcafbfd147b6

Terms of use

Copyright date:: 2004

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

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