Preparation of Achiral and of Enantiopure Geminally Disubstituted β-Amino Acids for β-Peptide Synthesis

Abele, Stefan; Seebàch, Dieter

doi:10.1002/(sici)1099-0690(200001)2000:1<1::aid-ejoc1>3.0.co;2-6

Cited by 293 publications

(135 citation statements)

References 168 publications

(57 reference statements)

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“…[315,347] The ArndtϪEistert homologation of α,α-disubstituted α-amino acids, 466 Ǟ 468, suffers from severe problems with both the preparation of diazo ketones 467 and their subsequent photolytic rearrangement (Scheme 56). [348] Diazo ketones 469, obtained by alkylation (KHDMS, HMPA, R 2 X) of 95, rearranged to give α-substituted β-amino acids 470 with moderate diastereoselectivity (anti/syn ഠ 6). [ more selective approach to anti-470 involves alkylation of β-amino esters 427 while repeated alkylation afforded 471.…”

Section: Homologation Of α-Amino Acidsmentioning

confidence: 99%

100 Years of the Wolff Rearrangement

2002

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The conversion of α‐diazo ketones into ketenes, and products derived therefrom, was discovered by Wolff in 1902. Major applications of the Wolff rearrangement, such as the Arndt−Eistert reaction (homologation of carboxylic acids) and the ring contraction of cyclic ketones, have been with us for some while. Nevertheless, substantial progress has been made recently. The reaction mechanism has been explored by means of matrix isolation, time‐resolved spectroscopy, and computation. Full retention of configuration of the migrating group has been established by using enantioselective chromatography. The Arndt−Eistert reaction has witnessed a renaissance in the field of natural products, in particular β‐amino acids and β‐peptides. Ring‐contracting Wolff rearrangements and ketene cycloadditions have been applied in syntheses of increasingly complex, biologically active target molecules. These accomplishments, as well as unsolved problems, are addressed in the present review. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Section: Homologation Of α-Amino Acidsmentioning

confidence: 99%

100 Years of the Wolff Rearrangement

2002

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“…12.017. new class of b-amino acids [27][28][29]. Especially the solidstate structures of the b-(hydrogen)glutamates ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Interactions of a β-dipeptide with monovalent metal cations: crystal structures of (anthranoyl)anthranilic acid and its lithium, sodium and thallium salts☆

Wiesbrock

Schmidbaur

2004

Journal of Inorganic Biochemistry

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“…[18][19][20] Conformational studies of β-amino acid oligomers are also currently at the focus of interest. [21][22][23][24] Besides their diverse chemical compositions, β-amino acids and their derivatives possess noteworthy pharmacological effects; for example, (1R,2S)-2-aminocyclopentanecarboxylic acid (cispentacin) and some other alicyclic β-amino acids have marked antifungal activity. 25 The present work describes a mild and efficient ring opening of monoterpene-fused β-lactam enantiomers derived from (+)-and (-)-α-pinene, to produce a novel chiral β-amino acid and its derivatives.…”

Section: -8mentioning

confidence: 99%