Journal
HELVETICA CHIMICA ACTA
Volume 105, Issue 11, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.202200110
Keywords
amino acids; cascade reactions; cyclization; heterocycles; organocatalysis
Categories
Funding
- Austrian Science Funds (FWF) [P31784]
- European Union [M00146]
- Austrian Science Fund (FWF) [P31784] Funding Source: Austrian Science Fund (FWF)
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We describe a protocol for the asymmetric aldol-initiated cascade addition of isoxazolidin-5-ones to ortho-cyanobenzaldehydes using Takemoto's bifunctional organocatalyst. This method allows for the synthesis of novel beta(2,2)-amino acid-phthalide conjugates with good enantio- and diastereoselectivities in reasonable yields, and the subsequent ring-opening of these compounds to acyclic carboxylic acid derivatives was demonstrated.
We herein report a protocol for the asymmetric aldol-initiated cascade addition of isoxazolidin-5-ones to ortho-cyanobenzaldehydes by using Takemoto's bifunctional organocatalyst. This approach allows for the synthesis of various novel beta(2,2)-amino acid-phthalide conjugates with good enantio- and diastereoselectivities in reasonable yields and the further ring-opening of these compounds to acyclic carboxylic acid derivatives was demonstrated too.
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