265669-27-0Relevant academic research and scientific papers
An asymmetric synthesis of α-amino acid derivatives from racemic ethyl N-phenylsulphonyl-α-bromoglycinate using homochiral aluminium complexes
Morgan, Paul E.,Whiting, Andrew,McCague, Ray
, p. 4795 - 4796 (1996)
Reactions of a racemic α-bromoglycinate 2 with readily available alkyl aluminium reagents modified by binaphthol derivatives produce α-amino acid analogues 3 in high yields and with asymmetric induction of up to 62%.
11-Beta HSD1 inhibitors
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Page/Page column 35, (2008/06/13)
This invention relates to inhibiting 11-beta HSD1.
Asymmetric α-substitution versus aza Diels-Alder reaction of electron deficient N-sulfonyl imines
Morgan, Paul E.,McCague, Ray,Whiting, Andrew
, p. 515 - 525 (2007/10/03)
Several N-arylsulfonylglycine esters have been brominated under photolytic conditions to provide the corresponding α-bromoglycine. These bromo esters can be treated with a range of bases to generate N-sulfonyl imino esters in situ; attempts to isolate the imines in a pure state were universally unsuccessful. Once generated, the imines can be trapped with cyclopcntadiene to provide the corresponding aza Diels-Alder adducts in varying yields, depending upon the base used. In addition, if organometallic bases were employed (alkyllithiums and alkylaluminium reagents), not only were aza Diels-Alder adducts formed, but addition to the imine was also observed. In the case of organoaluminium reagents, imine addition was the major product. This process could be transformed into a stoichiometric asymmetric version, by generating a chiral aluminium reagent in situ to form a trialkyl (or trialkoxy) aluminium reagent, which when reacted with an N-sulfonyl bromoglycinate resulted in 19 to 62% enantiomeric excess of the corresponding substituted glycinate product. The Royal Society of Chemistry 2000.
