The Journal of Organic Chemistry

Regioselective. alpha.-lithiation of unsymmetrical 1-(tert-butoxycarbonyl)-1, 4-dihydropyridines

DL Comins, MA Weglarz

Index: Comins, Daniel L.; Weglarz, Michael A. Journal of Organic Chemistry, 1988 , vol. 53, # 19 p. 4437 - 4442

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Citation Number: 19

Abstract

Table 111. Lithiation-Methylation of 1.4-Dihsdroovridine 4b yield of 11 ratio of 11 entry" baseb metalation conditionsC and 12:% to 12e a n-BuLi-78" C, 1 h 55 f 85: 15 b sec-BuLi- 78" C, 1 h 82 57: 43 c sec-BuLi-78" C, 1 h;-42" C, 1 h 85 53: 47 d sec-BuLig-78" C, 1 h;-42" C, 1 h 801 1oo: oe t-BuLi-78" C, 1 h 681 43: 57 g PhLi-42" C, 2 h 87 1oo: oh PhLi-78" C, 1 h 40f 95: 5 i PhLi-78 OC, 3 h 511 1000 f PhLi-42" C, 1 h 92 98: 2 j MesLi-78" C, 1 h 83 58: 42