. Author manuscript; available in PMC: 2012 Jun 17.

Published in final edited form as: J Org Chem. 2011 May 24;76(12):5092–5103. doi: 10.1021/jo200780x

Table 7.

Possible Diasteoselective 1,3-Sulfonyl Shift.

entry	ynamides^a	nitriles	yield^b	dr
1	(±)-69a: P = TIPS (±)-69b: P = Ac	74 75	91	1.5:1
2	(±)-69a: P = TIPS (±)-69b: P = Ac	74 75	50^c	1.3:1
3	(±)-69c: P = TIPS (±)-69d: P = Piv	76 77	≥95	2.0:1
4	(±)-69c: P = TIPS (±)-69d: P = Piv	76 77	69^c	1.5:1

Conditions: Toluene, 110 °C, and 2–4 h.

Isolated yields.