Journal article

Highly diastereoselective oxy-Michael additions of enantiopure delta-lactol anions to nitroalkenes: asymmetric synthesis of 1,2-amino alcohols.

Abstract:: The "naked" alkoxide 1 of (S)-6-methyl-δ-lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy-Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2-amino alcohol products. R1 = alkyl, aryl, furanyl, thiophenyl; R2,R 3 = -(CH2)3CHCH3O-.

Publication status:: Published

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APA Style

Adderley, N., Buchanan, D., Dixon, D., & Lainé, D. (2003). Highly diastereoselective oxy-Michael additions of enantiopure delta-lactol anions to nitroalkenes: asymmetric synthesis of 1,2-amino alcohols. Angewandte Chemie (International Ed. in English), 42(35), 4241–4244.

MLA Style

Adderley, N., et al. “Highly Diastereoselective Oxy-Michael Additions of Enantiopure Delta-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols.” Angewandte Chemie (International Ed. in English), vol. 42, no. 35, 2003, pp. 4241–44.

Chicago Style

Adderley, N, D Buchanan, D Dixon, and D Lainé. 2003. “Highly Diastereoselective Oxy-Michael Additions of Enantiopure Delta-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols.” Angewandte Chemie (International Ed. in English) 42 (35): 4241–44.
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Publisher copy:: 10.1002/anie.200352007

Authors

+ Adderley, N More by this author

Role:: Author

+ Buchanan, D More by this author

Role:: Author

+ Dixon, D More by this author

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

+ Lainé, D More by this author

Role:: Author

Journal:: Angewandte Chemie (International ed. in English) More from this journal
Volume:: 42
Issue:: 35
Pages:: 4241-4244
Publication date:: 2003-09-01
DOI:: 10.1002/anie.200352007
EISSN:: 1521-3773
ISSN:: 1433-7851

Language:: English
Keywords:: Stereoisomerism

Nitro Compounds

Alkenes

Anions

Models, Chemical

Amino Alcohols

Molecular Structure
Pubs id:: pubs:52056
UUID:: uuid:4b648aa1-9c38-48d4-a006-975b66457e00
Local pid:: pubs:52056
Source identifiers:: 52056
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2003

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

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