Acylation of Alcohols, Part 2: with Other Acylating Reagents скачать в хорошем качестве

Acylation of Alcohols, Part 2: with Other Acylating Reagents

This video is about the acylation of alcohols with other electrophiles than acyl halides, such as anhydrides, vinyl esters, imidazolides, and other esters. At the end there will also be some examples of enantioselective acylations that can be used to prepare enantiomerically enriched esters or alcohols. Further examples: Anhydrides: Org. Lett. 2020, 22, 3749-3754 (diols); ACS Catal. 2018, 8, 1067-1075 (asym); J. Org. Chem. 2018, 83, 2504-2515 (asym); 2017, 82, 869-886 (asym); Org. Syn. 2017, 94, 292 (asym); Org. Lett. 2017, 19, 2953-2956 (asym); ACS Catal. 2016, 6, 1165-1171 (asym); Bull. Chem. Soc. Jpn. 2016, 89, 1081-1092 (asym); J. Org. Chem. 2015, 80, 3159-3169 (asym); Org. Lett. 2014, 16, 236-239 (DMAP-HCl); Org. Syn. 2014, 91, 293 (DMAP); 39 (ArOH); 2012, 89, 143 (DMAP); Org. Proc. Res. Dev. 2012, 16, 1312-1316 (asym, enzymatic); J. Org. Chem. 2012, 77, 1722-1737 (asym); J. Am. Chem. Soc. 2012, 134, 15149-15153 (asym); Org. Proc. Res. Dev. 2008, 12, 192-195 (asym, enzymatic); Synthesis 2008, 267-268 (phosphomolybdic acid); Org. Lett. 2007, 9, 37-40 (amidines); Org. Proc. Res. Dev. 2007, 11, 609-615 (asym); J. Am. Chem. Soc. 2007, 129, 14775-14779 (DMAP); Org. Syn. 2007, 84, 68 (Montmorillonite); 2005, 81, 1 (pyridine); J. Am. Chem. Soc. 2004, 126, 12226-12227 (asym); Synthesis 2004, 111-115 (Cu(BF4)2); J. Org. Chem. 2004, 69, 577-580 (Al2O3); 2003, 68, 3844-3848 (asym); Tetrahedron 2002, 58, 1369-1374 (Cu(OTf)2); J. Org. Chem. 2001, 66, 5522-5527 (asym, tert-ROH); Org. Syn. 2000, 77, 45 (diol, Sc(OTf)3); J. Org. Chem. 1998, 63, 2342-2347 (TfOSiMe3); 1996, 61, 4560-4567 (Sc(OTf)3); Org. Syn. 1962, 42, 4 (pyridine); 1961, 41, 79 (ZnCl2); 1955, 35, 49 (H2SO4); 1948, 28, 68 (ArOH, H2SO4); 1942, 22, 56 (pyridine); 1 (H2SO4). Oxime esters: Org. Proc. Res. Dev. 2003, 7, 951-953 (asym, enzymatic). Thioesters: Org. Syn. 1988, 66, 108 (Ag+). Vinyl esters: Org. Lett. 2014, 16, 5952-5955 (asym, enzymatic); Org. Syn. 2012, 89, 420 (asym, enzymatic); 2005, 82, 43 (asym, enzymatic); Org. Lett. 2005, 7, 1347-1349 (asym, NHC); Org. Proc. Res. Dev. 2004, 8, 283-286 (asym, enzymatic); 229-237 (asym, enzymatic); 2002, 6, 138-145 (asym, enzymatic); Org. Lett. 2002, 4, 1607-1610 (asym); J. Org. Chem. 2002, 67, 4978-4981 (diols, enzymatic); 2001, 66, 3384-3396 (asym, enzymatic); Org. Syn. 1998, 75, 78 (asym, enzymatic); J. Org. Chem. 1996, 61, 2332-2336 (asym, enzymatic); EP 0357009 (1990, asym, enzymatic). Transesterification: Org. Proc. Res. Dev. 2017, 21, 1253-1258 (KOMe); 947-955 (thermal); J. Am. Chem. Soc. 2015, 137, 3996-4009 (asym, review); J. Org. Chem. 2002, 67, 1781-1785 (asym, enzymatic); Org. Lett. 2002, 4, 3583-3586 (NHC); Org. Syn. 1993, 71, 39 (H2SO4); Chem. Rev. 1993, 93, 1449-1470 (review); Org. Syn. 1989, 67, 170 (NaOEt); Tetrahedron Lett. 1986, 27, 2383-2386 (R3SnOSnR3); US 4289896 (1981, RPO(OH)2, 200 °C); Synthesis 1981, 142-143 (ISiMe3); 789-790 (Al2O3); 1973, 790-791 (KCN); Org. Syn. 1946, 26, 18 (TsOH); 1940, 20, 67 (H2SO4). Thiazolidines: J. Org. Chem. 1999, 64, 9365-9373 (asym). Imides: Org. Lett. 2018, 20, 5622-5625 (K3PO4). Diacyldisulfides: Org. Lett. 2016, 18, 5584-5587 (DMAP, ArOH). Acyl cyanides: J. Am. Chem. Soc. 2016, 138, 6002-6009 (diols).