Table 1.

Grignard Addition-Alkylations to Cyclic Oxonitriles

entry	oxonitrile	electrophile	cyclic nitrile	yielda (ratio)b
1		Mel		49%a (3.4:1)
2				55%a
3				51%a
4				47%a
5				49%c
6				61%d (1.8:1)
7		Mel		86%e
8				61%e
9				71%e (1.7:1)
10		Mel		50%f
11				24%
12				28%

^aStereochemistry assigned by x-ray crystallography.¹⁹

^bDiastereomeric ratio at the nitrile-bearing carbon with the major isomer shown.

^cThe stereochemical assignment is made by analogy to the acylation with t- BuCOCl, entry 4.

^dThe stereochemistry of the major isomer is unknown and is made by analogy.

^eIncluded for comparison from reference ⁹.

^fStereochemical assignment is based on the characteristic ¹³C shift of the nitrile carbon.²⁰