S. Hanessian, Pour un exemple de déprotection de NHAc en présence d'un acide de Lewis, Tetrahedron Lett, vol.16, pp.1549-1552, 1967.

Q. Xiao, J. Jin, X. Wang, J. Hu, and M. Xi, Synthesis, identification, and biological activity of metabolites of two novel selective S1P1 agonists, Bioorganic & Medicinal Chemistry, vol.24, issue.10, pp.2273-2279, 2016.
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D. D. Keith, J. A. Tortosa, and R. Yang, Synthesis of L-2-amino-4-methoxy-trans-but-3-enoic acid, The Journal of Organic Chemistry, vol.43, issue.19, pp.3711-3713, 1978.
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P. R. Sultane, T. B. Mete, and R. G. Bhat, Chemoselective N-deacetylation under mild conditions, Org. Biomol. Chem., vol.122, issue.2, pp.261-264, 2014.
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. Hz, 1.98 (s, 3 H, H10), 1.93 (s, 3 H, H12), pp.75-76

. Hz, 86 (s, 3 H, H14), pp.4-49

. Hz, 37 (s, 3 H, H11), 3.35 (s, 3 H, H11), H3), 2.11-1.91 (m, 1 H, H2), 1.24 (s, 9 H, H9), pp.3-441723

. Hz, 07 (s, 3 H, H11), 1.98 (s, 3 H, H9), 1, H4), 2.42 (d, J = 2.2 Hz, 1 H, H7), pp.4-27

. Hcl, 12 mmol, 6 equiv) After 2 h 40 of stirring an aqueous solution of NaHCO3 (30 mL) was added and stirred for 10 min. The layers were separated and the aqueous one was extracted with AcOEt (3 × 10 mL) The combined organic layers were washed with water (25 mL) and brine (20 mL), dried over anhydride MgSO4 and concentrated in vacuo to give a yellow oil, Et2O, 6 mL The residue was taken up in dry CH2Cl2

. Hz, 97-1.93 (m, 2 H, H8), 1.94 (s, 3 H, H13), pp.4-47

F. Nmr, 5 MHz, CDCl3): ? ?75.9 (s, 3 F)

F. Nmr, 5 MHz, CDCl3): ? ?75.8 (s, 3 F)

. Equiv, The solution was left to stir at ?80 °C for 1 h before adding iodomethane (6.37 mL, 102.3 mmol, 3 equiv) Without removing the acetone-liq. nitrogen bath the reaction was left to stir overnight (17 h) before adding water (20 mL) The layers were separated and the aqueous one was extracted with Et2O (3 x 10 mL) The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was filtred over a pad of silica gel, p.151

Z. Wang, G. Cao, and Y. Shi, Chiral Ketone Catalyzed Highly Chemo- and Enantioselective Epoxidation of Conjugated Enynes, The Journal of Organic Chemistry, vol.64, issue.20, pp.7646-7650, 1996.
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DOI : 10.1021/jo00434a009

C. To, 015 mmol, 5 mol%) in toluene (1 mL) was added a solution of 340 (33 mg, 0.30 mmol, 1 equiv) in toluene (0.5 mL) followed by a solution of B2Pin2 (80 mg, 0.315 mmol, 1.05 equiv) in toluene (0.5 mL). The reaction was left to stir overnight (24 h) and then was quenched with a 2:1 mixture of a sat

M. E. Piotti and H. Alper, Carbonylation of Alkynyl Epoxides:?? Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives, The Journal of Organic Chemistry, vol.62, issue.24, pp.8484-8489, 1997.
DOI : 10.1021/jo971303n

V. N. Lindsay, H. M. Viart, -. Sarpong, and R. , -Heterotricycles, Journal of the American Chemical Society, vol.137, issue.26, pp.8368-8371, 2015.
DOI : 10.1021/jacs.5b04295

URL : https://hal.archives-ouvertes.fr/in2p3-00556666

C. To, 5 mol%) in toluene (1 mL) was added a solution of 352 (79.3 mg, 0.25 mmol, 1 equiv) in toluene (0.5 mL) followed by a solution of B2Pin2 (66.7 mg, 0.263 mmol, 1.05 equiv) in toluene (0.5 mL) The reaction was left to stir overnight (18 h) and then was quenched with a 2:1 mixture of a sat. aq. NH4Cl solution and NH3 (28% H2O) The layers were separated and the aqueous one was extracted with Et2O. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel to afford pure 353 and 354 The analytical data were in agreement with those reported, 40%) as an orange solid, pp.351-155

. Allénylsilanes-ont-Été-développées, Ces deux voies reposent sur la réaction du tris(diméthylphényl)zincate de lithium avec les N-tert-butanesulfinylaziridines acétyléniques d'une part

. Finalement, -sulfinamido-et 4-sulfonylamido-1-allénylzincs par réarrangement métallate-1,2 de tris(diméthylphényl)zincates de lithium acétyléniques, obtenus à partir des N-tertbutanesulfinyl-et N-tert-butanesulfonylaziridines, se sont révélées infructueuses. En revanche, dans le cadre d'une collaboration franco-belge, l'étude de la borylation cupro-catalysée d'époxydes acétyléniques a donné des résultats prometteurs et a

. Finally, 4-sulfonylamido-1-allenylzincs through the 1,2- metalate rearrangement of acetylenic lithium tris(dimethylphenylsilyl)zincates, obtained from N-tertbutanesulfinyl-and N-tert-butanesulfonylaziridines, were proven to be unsuccessful. However, in the context of a French-Belgian collaboration, the study of the copper-catalyzed borylation of acetylenic epoxides led to promising results and paved the way for a new stereoselective synthesis of 4-hydroxy-1-allenylboranes