1999
DOI: 10.1021/jo9819739
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Abstract: The reaction of lithium enolates of achiral N-protected glycine esters with chiral alkoxyalkenylcarbene complexes of chromium provided the corresponding Michael adducts with either high anti or syn selectivity depending on the nature of the nitrogen protecting group, and high diastereofacial selectivity when carbene complexes containing the (-)-8-phenylmenthyloxy group were employed. Subsequent oxidation of the metal-carbene moiety followed by deprotection of the amine group and hydrolysis of both carboxylic e… Show more

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Cited by 54 publications
(36 citation statements)
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“…N-methyl nitrones 2 [28] and hydrazonoyl halides 11, [29] precursors of nitrilimines 10, were prepared according to previously described procedures. Fischer carbene complexes 1, [30] 8a, [25b] 8b, [31] 8c, [8a] 16, [8a] and 19a,b [25b] were prepared as described. -Solvents were dried by standard methods.…”
Section: Methodsmentioning
confidence: 99%
“…N-methyl nitrones 2 [28] and hydrazonoyl halides 11, [29] precursors of nitrilimines 10, were prepared according to previously described procedures. Fischer carbene complexes 1, [30] 8a, [25b] 8b, [31] 8c, [8a] 16, [8a] and 19a,b [25b] were prepared as described. -Solvents were dried by standard methods.…”
Section: Methodsmentioning
confidence: 99%
“…Using 2 equivalents of a racemic alkylbromide, a kinetic resolution has been observed by Davies et al, leading to amino 76 By playing on the structure of the lithium glycine enolates, both syn and anti amino acids have been obtained in good yields and selectivities (Scheme 20).…”
Section: Chiral Glycine Enolatesmentioning
confidence: 96%
“…The diastereosective Michael-type addition of glycine anions 62 and 64 to chiral alkenylcarbene complexes is described in Scheme 22 [38]. Conventional oxidation of the carbene function in 63 and 64 allows their transformation into the corresponding optically active -substituted glutamic acids.…”
Section: Scheme 21mentioning
confidence: 99%