192876-25-8Relevant academic research and scientific papers
Oxazinanones as chiral auxiliaries: Synthesis and evaluation in enolate alkylations and aldol reactions
Davies, Stephen G.,Garner, A. Christopher,Roberts, Paul M.,Smith, Andrew D.,Sweet, Miles J.,Thomson, James E.
, p. 2753 - 2768 (2006)
Homochiral β-amino esters (prepared on multigram scale by lithium amide conjugate addition) are readily transformed into oxazinanones. N-Acyl derivatives of oxazinanones undergo stereoselective enolate alkylation reactions, with higher stereoselectivities observed for the enolate alkylation of (R)-N-propanoyl-4-iso-propyl-6,6-dimethyl-oxazinan-2-one than the corresponding Evans oxazolidin-2-one. A C(4)-iso-propyl stereodirecting group within the oxazinanone conveys higher stereoselectivity than the analogous C(4)-phenyl substituent. gem-Dimethyl substitution at C(6) within the oxazinanone framework facilitates exclusive exocyclic cleavage upon hydrolysis to furnish α-substituted carboxylic acid derivatives and the parent oxazinanone in good yield. Asymmetric aldol reactions of a range of aromatic and aliphatic aldehydes with the chlorotitanium enolate of (R)-N-propanoyl-4-iso- propyl-6,6-dimethyl-oxazinan-2-one proceed with excellent diastereoselectivity. Hydrolysis of the aldol products affords homochiral α-methyl-β- hydroxy-carboxylic acids. The Royal Society of Chemistry 2006.
