2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones

An Overview of Highly Optically Pure Chloramphenicol Bases: Applications and Modifications

“…In addition, several hydroxyl protective groups were introduced by Sztaricskai. The results indicated that cis-α/β-ratio could be influenced by the protective groups of the diol moiety of ANP and removal of the N-auxiliary moiety could be accomplished by direct oxidation [41].…”

Asymmetric Synthesis of β-Lactams by Staudinger Ketene-Imine Cycloaddition Reaction

“…[1] The constant need for new drugs dismost widely employed family of antimicrobial agents to playing broader antibacterial activity and the necessity for date, the β-lactam antibiotics, which include as representanew β-lactam antibiotics to combat the microorganisms that have built up a resistance against the most traditional The most recent examples exploiting the use of imines the development of new β-lactam inhibitors for related serderived from chiral amines have been reported indepenine protease targets like β-lactamases and elastases. [14] For instance (Scheme 2), As a consequence, a large number of chemical methods it has been found that the imine 10, derived from the amino for the production of β-lactams have been developed and acid -threonine, upon treatment with azidoacetyl chloride the topic has been amply documented and reviewed several and triethylamine affords β-lactams 11/12 in a 95:5 stereotimes. [14] For instance (Scheme 2), As a consequence, a large number of chemical methods it has been found that the imine 10, derived from the amino for the production of β-lactams have been developed and acid -threonine, upon treatment with azidoacetyl chloride the topic has been amply documented and reviewed several and triethylamine affords β-lactams 11/12 in a 95:5 stereotimes.…”

Asymmetric electrocyclic reactions

“…Enantiomerically-enriched imines derived from both chiral aldehydes and amines have been shown to be effective in controlling the diastereoselectivity of the Staudinger reaction. A number of chiral amines have been utilized to this end, including those derived from D-threonine, 107 L-threonine, 108 phenylethylamine, 109,110 L-alanine, 111 and (2S,5S)-2,5-hexanediol. 112,113 The last example is noteworthy since it employs a chiral hydrazone yielding N-amino b-lactams with very high diastereoselectivity and an interesting temperature-dependence (Scheme 17).…”