236110-99-9Relevant academic research and scientific papers
Non-thiazolidinedione antihyperglycaemic agents. Part 4: Synthesis of (±)-, (R)-(+)- and (S)-(-)-enantiomers of 2-oxy-3-arylpropanoic acids
Haigh, David,Birrell, Helen C.,Cantello, Barrie C. C.,Hindley, Richard M.,Ramaswamy, Anantha,Rami, Harshad K.,Stevens, Nicola C.
, p. 1335 - 1351 (2007/10/03)
The synthesis of a new series of potent 2-oxy-3-arylpropanoic acid antihyperglycaemic agents in both racemic and non-racemic form is described. Resolution of racemic acids 1 is accomplished via amide formation with either (S)-2-phenylglycinol or (S)-4-benzyloxazolidin-2-one as complementary resolving agents.
Non-thiazolidinedione antihyperglycaemic agents. Part 5: Asymmetric aldol synthesis of (S)-(-)-2-oxy-3-arylpropanoic acids
Haigh, David,Birrell, Helen C.,Cantello, Barrie C. C.,Eggleston, Drake S.,Haltiwanger, R. Curtis,Hindley, Richard M.,Ramaswamy, Anantha,Stevens, Nicola C.
, p. 1353 - 1367 (2007/10/03)
Boron-mediated asymmetric aldol reactions of substituted benzaldehyde 5 with 2-oxyethanoyloxazolidinones 4a-e, containing electron withdrawing, chelating, and bulky alkoxy and aryloxy groups, gave variable yields of syn- aldol adducts 6a-e in high diastereoisomeric excess. Dehydroxylation of these adducts afforded 7a-e in a sequence which complements the traditional Evans asymmetric alkylation strategy. Cleavage of the auxiliary from 7a-e afforded antihyperglycaemic (S)-(-)-2-oxy-3-arylpropanoic acids 3a-e in excellent enantiomeric excess.
