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. Author manuscript; available in PMC: 2020 Jul 24.
Published in final edited form as: J Am Chem Soc. 2019 Jul 11;141(29):11414–11419. doi: 10.1021/jacs.9b05556

Table 1.

Reaction Scopea

graphic file with name nihms-1591812-t0006.jpg
a

Conditions: substrate (0.5 mmol), catalyst (0.0125 mmol), nucleophile (1.0 mmol), 3 Å MS (60 mg), DCM (2 mL), under N2, initially cooled to −78 °C and stirred at −30 °C, 36 h. Enantiomeric excess determined by HPLC. Diastereomeric ratio determined by 1H NMR of the crude product, yield reflects isolation of major diasteromer.

b

−5 °C.

c

catalyst (0.05 mmol), nucleophile (2.0 mmol), DCM (5 mL), −50 °C, 72 h.

d

catalyst (0.05 mmol), nucleophile (1.5 mmol), DCM (5 mL), −30 °C, 72 h.

e

(E)-trimethyl(2-methylbut-2-en-1-yl)silane and (E)-crotylstannane employed as the nucleophiles. Yields and enantioselectivities in parentheses are of crystallized products.