Use of an ephedrine alkoxide to mediate enantioselective addition of an acetylide to a prochiral ketone: asymmetric synthesis of the reverse transcriptase inhibitor L- …
…, EG Corley, MF Huntington, EJJ Grabowski
Index: Thompson, Andrew S.; Corley, Edward G.; Huntington, Martha F.; Grabowski, E. J. J. Tetrahedron Letters, 1995 , vol. 36, # 49 p. 8937 - 8940
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Citation Number: 136
Abstract
Experimental Conditions: The (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)propan-1-ol (33 g, 161 mmol) was dissolved in dry THF(140 mL) and cooled to −15°C. To the mixture at −15°C under N 2 was added neat cyclopropyl-acetylene ( 15.0 mL at ca, 90% purity, 160 mmol) and n-butyllithium (2.5M in hexanes, 125 mL, 312 mmol) dropwise. The mixture was aged at −5° to 0°C for 30 minutes, then cooled to −55°C. The ketone (25 gm, 72.8 mmol) in THF (60 mL) was ...
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