Deprotonation of chelating enamines. Direct formation of. beta.-lithio enamines

G Stork, CS Shiner, CW Cheng…

Index: Stork, Gilbert; Shiner, Christopher S.; Cheng, Chi-Wen; Polt, Robin L. Journal of the American Chemical Society, 1986 , vol. 108, # 2 p. 304 - 305

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Citation Number: 14

Abstract

9 product that would be obtained from either anion 2 or 2'. The proof that the unexpected 2 is actually the correct structure came from examination of the methylated enamine 7 itself MS (CI, methane), m/e 197 (M+ 1); bp (Kugelrohr) 90" C (2 mm); NMR 1.65 (3 H, s, C= CCH,; no vinyl hydrogen); IR 1675 cm-'. Similarly, deuteration of the enamine anion (3 equiv of D20,- 40 OC) gave only 8: no vinyl hydrogen in NMR; IR 2260 cm-'(C= CD), no absorption at ...