Journal
ORGANIC LETTERS
Volume 11, Issue 18, Pages 4056-4059Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol901483x
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- The Ministry of Education, Culture, Sports, Science, and Technology (MEXT)
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Diphenylprolinol silyl ether was found to be an effective organocatalyst in the enantioselective and direct Michael reaction of nitroethanol and alpha,beta-unsaturated aldehydes, affording the 1-hydroxy-trans-3,4-disubstituted tetrahydropyrans after isomerization. The generated Michael addition products are useful synthetic Intermediates, which can be converted Into chiral tetrahydropyran with a quaternary stereocenter, 3-substituted cis- and trans-prolines, and alpha-amino acid derivatives.
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