Convenient preparation and manipulation of Me3SnH from Me3SnCl. Formation and use of mixed trimethylstannylcuprates via transmetalation reactions

Catalytic Enantioselective Hydrostannation of Cyclopropenes.

“…Yield 3.323 g (22.7 mmol, 91%). 1 H NMR (500.13 MHz, CDCl 3 ) δ 7.35 (s, 2H), 7.33 (t, 2H), 7.25 (d, 2H), 7.21 (t, 1H), 4.09 (s, 2H), 1.53 (br. s, 1H); 13 C NMR (125.76 MHz, CDCl 3 ) δ 145.7, 128.2 (+, 2C), 126.3 (+, 2C), 125.9 (+), 113.1 (+, 2C), 67.9 (-), 29.1.…”

“…Yield 925 mg (4.86 mmol, 80%). 1 [1-Phenylcycloprop-2-en-1-yl]methyl acetate (1e). To a stirred solution of alcohol 4 (1.00 g, 6.84 mmol) and dry pyridine (1.2 mL) in anhydrous CH 2 Cl 2 (10 mL) was added acetic anhydride (1.0 mL).…”

“…Yield: 1.043 g (5.54 mmol, 81%). 1 H NMR (500.13 MHz, CDCl 3 ) δ 7.34-7.31 (m, 2H), 7.25 (s, 2H), 7.24-7.20 (m, 3H), 4.55 (s, 2H), 2.07 (s, 3H); 13 C NMR (125.76 MHz, CDCl 3 ) δ 171.2, 145.5, 128.2 (+, 2C), 126.2 (+, 2C), 125.8 (+), 112.0 (+, 2C), 71.2 (-), 25.9, 21.1 (+); GC/MS m/z 188 (M + , 1%), 145 (M + -CH 3 CO, 7%), 128 (M + -AcOH, 100%), 115 (M + -CH 2 OAc, 45%).…”

“…Yield: 1.082 g (5.87 mmol, 77%). 1 H NMR (500.13 MHz, CDCl 3 ) δ 7.14 (s, 2H), 3.96 (s, 2H), 2.01 (s, 2H), -0.07 (s, 9H); 13 C NMR (125.76 MHz, CDCl 3 ) δ 171.0, 112.7 (+, 2C), 73.5 (-), 21.0 (+), 12.6, -2.4 (+, 3C); 29 Si NMR (99.36 MHz, CDCl 3 ) δ 1.34;…”

“…Yield 1.171 g (5.22 mmol, 74%). 1 H NMR (500.13 MHz, CDCl 3 ) δ 7.15 (s, 2H), 5.65 (septet, J = 1.3 Hz, 1H), 3.99 (s, 2H), 2.14 (d, J = 1.3 Hz, 3H), 1.87 (d, J = 1.3 Hz, 3H), -0.06 (s, 9H); 13…”