Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine

Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine
Masato Kitamura, Shinji Tanaka, Ramachandran Gunasekar, Yusuke Suzuki, Tatsuya Tanaka, Yoko Iyoda
A new enantioselective catalysis has been developed for the one-step construction of methylene-bridged chiral modules of 1,2- and 1,3-OH and/or NH function(s) from δ- or λ-OH/NHBoc-substituted allylic alcohols and “H2C═O”/“H2C═NBoc”. A protonic nucleophile, either in situ-generated CH2OH or CH2NHBoc, is intramolecularly allylated to furnish eight possible 1,2- or 1,3-O,O, -O,N, -N,O, and -N,N chiral modules equipped with an ethenyl group in high yields and enantioselectivities. The utility of this method has been demonstrated in the five-step synthesis of sphingosine.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01181

DOI: 10.1021/acs.joc.7b01181

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