A facile access to peptides containing<scp>D</scp>-α-methyl β-alkylserines by coupling of α-branched leuchs anhydrides with α-amino esters

Palomo, C.; Aizpurua, J. M.; Urchegui, Raquel; Garcı́a, Jesús M.

doi:10.1039/c39950002327

Cited by 14 publications

(5 citation statements)

References 16 publications

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“…Remarkably, the bulky Aib-benzyl ester is also coupled with 121 to afford 125 in 79% yield. 47 The transformation of a-hydroxy b-lactams 127a-c, Scheme 37, readily available from the 4-formyl azetidin-2-one 126, into their corresponding NCA's illustrates the scope of the present approach. NCA's 128a and 128b upon treatment with (S)-PheOMe and (S)-ValOMe, in the presence of KCN as promoter, render dipeptides 129a and 130b in 78% and 71% yields, respectively.…”

Section: Nca's Of A-branched A-amino Acidsmentioning

confidence: 92%

β-Lactams as Versatile Intermediates in α- and β-Amino Acid Synthesis

Palomo¹,

Aizpurua²,

Ganboa³

et al. 2001

Synlett

156

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ACCOUNT 1813 b-Lactams as Versatile Intermediates in aand b-Amino Acid Synthesis b-Lactams a s V e r s a t i l e I n t e r m e d i a t e s i n a-a n d b-Amino A c i d S y n t h e s i s Abstract: The use of b-lactams as synthetic intermediates has recently found considerable interest, driven by the accessibility of enantiomerically pure b-lactam building-blocks and by the discovery of selective methods for the b-lactam ring opening. N 1 -C 2 and C 2 -C 3 bond cleavage of b-lactams can now be effected cleanly by different nucleophiles, in an intra-or intermolecular fashion, under isomerization-free conditions. By this way, an array of diverse, densely functionalized, cyclic as well as open chain, aand b-amino acid derivatives, including peptides, have been synthesized. Examples from our laboratory and from others are provided.

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Section: Nca's Of A-branched A-amino Acidsmentioning

confidence: 92%

β-Lactams as Versatile Intermediates in α- and β-Amino Acid Synthesis

Palomo¹,

Aizpurua²,

Ganboa³

et al. 2001

Synlett

156

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“…A convenient synthesis of enantiopure azetidine-2,3-diones as building blocks 14 and precursors 15 for functionalized b-lactams was published. 16 Chiral ketene precursors prepared from commercially available diethyl L-tartrate were used in a Staudinger cycloaddition with different imines to generate diastereomers of spiro-b-lactams in a ratio of about 60:40.…”

Section: (H) Scaffold For Azetidine-23-dionesmentioning

confidence: 99%

Diethyl Tartrate

Weiß¹

2011

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research Diethyl Tartrate Compiled by Christine WeissChristine Weiss was born in 1983 in Herten, Germany. She studied Chemistry at the Westfälische Wilhelms-University of Münster. After finishing her diploma thesis about chiral ion pair catalysis and asymmetric hydrogenation in the research group of Professor Dr. F. Glorius, Münster University, she is presently working towards her Ph.D. under the supervision of Professor Dr. N. Sewald at Bielefeld University. Her current research is focused on the synthesis of novel chemotherapeutics.

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“…12 One particularly important and useful class of synthons are substituted azetidine-2,3-diones. They have been shown to be promising building blocks 13 and precursors for highly functionalized blactams 14 including Sch-48461 and Sch-58235 which display an important cholesterol absorption inhibitory activity (Figure 1).…”

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confidence: 99%

“…17 However, besides this method few other methods are also available in the literature. [18][19][20][21] Most of the reports dealing with the applications of enantiopure azetidine-2,3diones [13][14][15][16] utilize the method of oxidation of corresponding 3-hydroxy b-lactams. Interestingly these chiral 3-hydroxy b-lactams have been synthesized starting with chiral imines.…”

mentioning

confidence: 99%