Diastereoselective Henry Reaction Catalyzed by Guanidine-Thiourea Bifunctional Organocatalyst
摘要:
A highly diastereoselective Henry reaction (diastereomer ratio of 84:16 to 99:1) of α-substituted aldehydes with nitromethane was developed using guanidine-thiourea bifunctional catalyst 1. N,N-Dibenzyl-protected α-amino aldehydes (2A, 2D-H) and α-hydroxy aldehydes protected as silyl ethers (2I-J) were suitable substrates. The matched combination of this catalytic system, i.e., S-aldehydes and (R,R)-1 catalyst, can be understood in terms of the transition state of the asymmetric version of the Henry reaction catalyzed by 1.
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关键词:
bifunctional organocatalyst guanidine thiourea Henry reaction diastereoselective reaction ASYMMETRIC NITROALDOL REACTION HETERO-MICHAEL REACTION ALPHA-AMINO ALDEHYDES STEREOSELECTIVE-SYNTHESIS PENTACYCLIC GUANIDINE NITROMETHANE CONCISE BASES
DOI:
10.1055/s-2005-922770
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