663169-50-4Relevant articles and documents
Studies of Azetidin-2-one as a Reactive Enolate Synthon of β-Alanine for Condensations with Aldehydes and Ketones
Williams, David R.,Donnell, Andrew F.,Kammler, David C.,Ward, Sarah A.,Taylor, Levin
, p. 10463 - 10475 (2016/11/17)
Studies describe formation of the lithium enolate of N-(4-methoxybenzyloxy)azetidin-2-one (1) and characterization of representative aldol reactions with aldehydes and ketones. Diastereoselectivity features the production of anti-aldol adducts from α,β-unsaturated ketones and α-branched aliphatic aldehydes. The stereoselectivity is rationalized via closed, six-membered transition-state arrangements leading to the formation of Felkin-Anh and anti-Felkin products. Examples illustrate the direct incorporation of monocyclic β-lactams into a variety of molecular architectures. The utility of 1 as an enolate synthon of homoglycine (β-alanine) is illustrated by the efficient synthesis of novel β-amino acid derivatives, including complex 4-hydroxy-2-pyridinones.
Aldol reactions of unsubstituted β-lactams. Studies of a β-glycine enolate equivalent
Williams, David R.,Donnell, Andrew F.,Kammler, David C.
, p. 167 - 172 (2007/10/03)
Aldol reactions of the lithium enolate of N-(4-methoxybenzyloxy)azetidin-2-one (1) were examined. High diastereoselectivity favoring the anti adduct was observed with achiral aldehydes. Modest α-stereocontrol with chiral aldehydes was realized. Application of this method for the efficient synthesis of novel β-amino esters is also described.
