Journal article

Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters.

Abstract:: [reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.

Publication status:: Published

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APA Style

Dixon, D., Ley, S., Polara, A., & Sheppard, T. (2001). Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters. Organic Letters, 3(23), 3749–3752.

MLA Style

Dixon, D., et al. “Highly Diastereoselective Lithium Enolate Aldol Reactions of Butane-2,3-Diacetal Desymmetrized Glycolic Acid and Deprotection to Enantiopure Anti-2,3-Dihydroxy Esters.” Organic Letters, vol. 3, no. 23, 2001, pp. 3749–52.

Chicago Style

Dixon, D, S Ley, A Polara, and T Sheppard. 2001. “Highly Diastereoselective Lithium Enolate Aldol Reactions of Butane-2,3-Diacetal Desymmetrized Glycolic Acid and Deprotection to Enantiopure Anti-2,3-Dihydroxy Esters.” Organic Letters 3 (23): 3749–52.
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Publisher copy:: 10.1021/ol016707n

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

+ Polara, A More by this author

Role:: Author

+ Sheppard, T More by this author

Role:: Author

Journal:: Organic letters More from this journal
Volume:: 3
Issue:: 23
Pages:: 3749-3752
Publication date:: 2001-11-01
DOI:: 10.1021/ol016707n
EISSN:: 1523-7052
ISSN:: 1523-7060

Language:: English
Keywords:: Alkylation

Stereoisomerism

Silanes

Lithium

Catalysis

Indicators and Reagents

Acetals

Esters

Lithium Compounds
Pubs id:: pubs:52048
UUID:: uuid:2ffaf9bc-b1cb-4b59-ab54-97cb1ab632ed
Local pid:: pubs:52048
Source identifiers:: 52048
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2001

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

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