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

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Hertweck,  Christian
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Boland,  Wilhelm
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Citation

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+.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0012-A0B0-8
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