α-Amino ester derivatives as nucleophiles in stereoselective palladium catalysed allylic substitution reactions

Baldwin, I. Craig; Williams, Jonathan M. J.; Beckett, R.Paul

doi:10.1016/0957-4166(95)00186-s

Cited by 39 publications

(3 citation statements)

References 14 publications

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“…a). 80 Similar results, with higher diastereoselectivities, have then been described by Kazmaier et al using a zinc chelated glycine enolate (Scheme 22, Eq. b and c).…”

Section: 22supporting

confidence: 77%

Stereocontrolled routes to β,β′-disubstituted α-amino acids

2009

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Owing to their significant abundance in natural products, chiral beta,beta'-disubstituted alpha-amino acids remain an important synthetic objective. Emphasis has been focused in this critical review on the great diversity of enantio- and diastereoselective methodologies to reach these highly functionalized compounds. The oldest and cutting edge synthetic methods are described in parallel with the synthesis of many relevant biologically active targets (224 references).

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“…a). 80 Similar results, with higher diastereoselectivities, have then been described by Kazmaier et al using a zinc chelated glycine enolate (Scheme 22, Eq. b and c).…”

Section: 22supporting

confidence: 77%

Stereocontrolled routes to β,β′-disubstituted α-amino acids

2009

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“…The combination of 17 with (Ϫ)-quinine led to an improvement to 11% ee for (ϩ)-ABS (double stereoselection). The phosphane oxazoline ligands 18Ϫ20 [47] [48] induced up to 99% ee in allylations in which the stereogenic center is formed in the allylic system and up to 13% ee in allylations in which the stereogenic center is formed in the nucleophile [49] [50] . In the catalytic allylation of BS with allyl acetate, an enantiomeric excess of only about 1% ee for (ϩ)-ABS was obtained.…”

Section: (Entry 3) Which Is Slightly Better Than the Enantioselectivmentioning

confidence: 99%

Enantioselective Palladium-Catalysed Allylation of 1,5-Dimethylbarbituric Acid

Brunner¹,

Deml

Dirnberger

et al. 1998

Eur. J. Inorg. Chem.

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“…4 Thus, the procedure of their catalytic asymmetric synthesis remains to be established. Imino esters as nucleophiles in Pd-catalyzed asymmetric allylic alkylation reactions give chiral a-monoalkylated amino acids, 5,6 however, the ee was not high when simple allyl acetate was used. Though a significant improvement of the asymmetric alkylation of a glycine Schiff's base under PTC conditions has been reported, an amino acid with a quaternary chiral centre could not be easily constructed in general.…”

Section: Received (In Cambridge Uk) 12th May 2000 Accepted 18th Augus...mentioning

confidence: 99%