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Text: Alkyne ( R)-25 was prepared by Grignard addition of SI-28 into 2 - naphthaldehyde . The resultant alcohol rac - SI-29 was oxidized and the ketone underwent enantioselective reduction and was alkylated . SI-26 . The TMS protected alkyne was prepared according to a modified procedure reported by Ramesh . 14 A flame - dried round bottom flask equipped with a stir bar was charged with 4pentyn-1 - ol ( 1.86 mL , 20.0 mmol , 1.00 equiv ) and THF ( 50 mL ) and cooled to -78 o C. n - Butyllithium ( 29 mL , 1.5 M in hexanes , 44 mmol , 2.2 equiv ) was slowly added to the flask and stirred for 1 h at -78 o C. TMSCl ( 7.6 mL , 60 mmol , 3.0 equiv ) was added and the reaction was allowed to warm slowly to ambient temperature overnight . The reaction was cooled to 0 o C and quenched with 2 M HCl and stirred at ambient temperature until the bis - silylated product was no longer present by TLC . The reaction mixture was then extracted with Et 2 O ( 3 x 40 mL ) , and the combined organic layers were washed with brine , NaHCO 3 and with brine once more before drying over MgSO 4 , filtration and concentration in vacuo . The product was purified by flash column chromatography ( 10 - 30 % EtOAc / hexanes ) to afford the title compound as a clear oil ( 2.64 g , 16.9 mmol , 84 % ) . The analytical data is consistent with literature values . 13   ( R)-SI-29 . Using representative procedure F outlined above , the following amounts of reagents were used : ketone SI-30 ( 0.84 g , 3.0 mmol , 1.0 equiv ) , ( S)-Me - CBS ( 68 mg , 0.30 mmol , 0.10 equiv ) , catecholborane ( 0.64 mL , 6.0 mmol , 2.0 equiv ) , and PhMe ( 25 mL ; SFC analysis ( OD - H , 12 % IPA , 2.5 mL / min ) indicated 93 % ee : t R ( major ) = 11.6 minutes , t R ( minor ) = 9.5 minutes .<|eot_id|><|start_header_id|>assistant<|end_header_id|>

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