Stereoselective Iodocyclization of (<i>S</i>)-Allylalanine Derivatives:  γ-Lactone vs Cyclic Carbamate Formation

Pattarozzi, Mariella; Zonta, Cristiano; Broxterman, Quirinus B.; Kaptein, Bernard; Zorzi, Rita De; Randaccio, Lucio; Scrimin, Paolo; Licini, Giulia

doi:10.1021/ol070764k

Cited by 25 publications

(7 citation statements)

References 31 publications

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“…However, the only product isolated was the Z isomer of the corresponding β‐iodo derivative, in 87 % yield. Recently, Licini et al described the iodocyclization of allylalanine derivatives to γ‐lactones and oxazolinones in good yields 12. According to the authors, the efficiencies of I 2 and N ‐iodosuccinimide (NIS) as I + sources appear to be comparable in terms of reactivity.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Substituted Oxazoles from N‐Acyl‐β‐hydroxyamino Acid Derivatives

2008

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Several N-acyl-β-hydroxyamino acids were prepared and treated with di-tert-butyl dicarbonate in the presence of 4-(dimethylamino)pyridine, followed by treatment with N,N,NЈ,NЈ-tetramethylguanidine to give the corresponding N-acyldehydroamino acids in good to high yields. These were then treated with I 2 /K 2 CO 3 followed by 1,8-diazabicyclo[5.4.0]undec-7-ene. The methyl esters of N-acyldehydroaminobutyric acid gave the corresponding substituted oxazoles in good to high yields. The N-acyldehydrophenylalanines gave 5-phenyloxazole derivatives in low to moderate yields together with β-iododehydrophenylalanines. Under the same conditions, N-acyldehydroalanines failed to give the corresponding oxazoles. However, when the reac-

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Section: Resultsmentioning

confidence: 99%

Synthesis of Substituted Oxazoles from N‐Acyl‐β‐hydroxyamino Acid Derivatives

2008

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“…Starting from ( S )‐allylglycine and‐alanine, N ‐Boc derivatives of benzyl and isopropyl esters ( 9a , b ) were synthesized (Scheme ). The reactions of 9a , b with NBS produces mixtures of isomeric bromourethanes 10a ( cis / trans = 1:2) and 10b ( cis / trans = 1:11), the configurations of which were assigned by analogy to the formation of iodourethanes in a similar reaction 12f. These bromides were also transformed into piperidine‐2,4‐diones 11a , b in high yields.…”

Section: Resultsmentioning

confidence: 98%

A New Method of Synthesis of 6‐Substituted Piperidine‐2,4‐diones from Homoallylamines

et al. 2011

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Mono-and dihomoallylamines serve as convenient precursors for the preparation of 6-substituted piperidine-2,4-diones. This transformation is based, on the one hand, on a simple and well-known halocyclocarbamation reaction proceeding by the addition of a source of cationic halogen to the N-Boc-protected homoallylamines and, on the other, on a new enolate-isocyanate rearrangement that proceeds by the action of strong bases on bromocyclocarbamates. A set of racemic dihomoallylamines were prepared by the allylboration of nitriles or primary amides with triallylborane and enantiomerically enriched N-Boc-1-phenyl-3-butenylamine was synthesized by the addition of (-)-AllB(Ipc) 2 to the corre-

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“…Traditional iodolactonization methods provided moderate to good yield of the desired lactone as a mixture of diastereomers (Table 3, entries 1-5) 23-26. Use of N -bromosuccinimide led to slightly improved diastereomeric ratios and decreased yield.…”

Section: Resultsmentioning

confidence: 99%