Journal article

Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives.

Abstract:: [reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to alpha,beta-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives alpha-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to gamma-lactams, which can be easily converted into alpha-hydroxy-gamma-amino acid derivatives.

Publication status:: Published

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APA Style

Dixon, D., Ley, S., & Rodríguez, F. (2001). Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives. Organic Letters, 3(23), 3753–3755.

MLA Style

Dixon, D, et al. “Highly Diastereoselective Michael Addition Reactions of Butane-2,3-Diacetal Desymmetrized Glycolic Acid. Preparation of Alpha-Hydroxy-Gamma-Amino Acid Derivatives.” Organic Letters, vol. 3, no. 23, 2001, pp. 3753–55.

Chicago Style

Dixon, D, S Ley, and F Rodríguez. 2001. “Highly Diastereoselective Michael Addition Reactions of Butane-2,3-Diacetal Desymmetrized Glycolic Acid. Preparation of Alpha-Hydroxy-Gamma-Amino Acid Derivatives.” Organic Letters 3 (23): 3753–55.
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Publisher copy:: 10.1021/ol016708f

Authors

+ Dixon, D More by this author

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

+ Ley, S More by this author

Role:: Author

+ Rodríguez, F More by this author

Role:: Author

Journal:: Organic letters More from this journal
Volume:: 3
Issue:: 23
Pages:: 3753-3755
Publication date:: 2001-11-01
DOI:: 10.1021/ol016708f
EISSN:: 1523-7052
ISSN:: 1523-7060

Language:: English
Keywords:: Lithium

Magnetic Resonance Spectroscopy

Silanes

Lithium Compounds

Indicators and Reagents

Acetals

Catalysis
Pubs id:: pubs:52049
UUID:: uuid:f36db92e-4479-41f4-a8f5-f5c0e6010254
Local pid:: pubs:52049
Source identifiers:: 52049
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_f36db92e447941f4a8f5f5c0e6010254

Terms of use

Copyright date:: 2001

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

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