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  Asymmetric alpha-chloroallylboration of amino aldehydes: A novel and highly versatile route to D- and L-erythro-sphingoid bases

Hertweck, C., & Boland, W. (1999). Asymmetric alpha-chloroallylboration of amino aldehydes: A novel and highly versatile route to D- and L-erythro-sphingoid bases. Journal of Organic Chemistry, 64(12), 4426-4430. doi:10.1021/jo990117+.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0012-A0B0-8 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0025-AA77-1
Genre: Journal Article

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BOL007.pdf (Publisher version), 0B
 
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 Creators:
Hertweck, Christian1, Author           
Boland, Wilhelm1, Author           
Affiliations:
1Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society, ou_24028              

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Free keywords: Stereoselective synthesis Acyclic vinyloxiranes Efficient synthesis Threo-sphingosine Sn2' additions L-serine Stereochemistry Sphingolipids Reagents Stereoisomers. Chemistry & Analysis in Current Contents(R)/Life Sciences. Organic Chemistry/Polymer Science in Current Contents(R)/Physical, Chemical & Earth Sciences.
 Abstract: Serinal-derived vinyloxiranes represent versatile building blocks for synthesis of D-(or L-)erythrosphingosine and, its analogues. Asymmetric alpha-chloroallylation of the Garner aldehyde with chiral and achiral gamma-(Z)-chloroallylboranes, followed by

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 Dates: 1999
 Publication Status: Issued
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 Identifiers: Other: BOL007
DOI: 10.1021/jo990117+
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Title: Journal of Organic Chemistry
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Source Genre: Journal
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Pages: - Volume / Issue: 64 (12) Sequence Number: - Start / End Page: 4426 - 4430 Identifier: -