Skip to main content
. Author manuscript; available in PMC: 2012 Oct 21.
Published in final edited form as: Org Lett. 2011 Sep 20;13(20):5420–5423. doi: 10.1021/ol201730q

Table 2.

Double-Michael Annulations of Various Dinucleophilesagraphic file with name nihms-326518-t0006.jpg

entry X,Y Z product yield (%)b
PMe3 DMAP
1 O, S (1b) H 4c 93
2 O, O (1c) H 4d 80
3 S, S (1d) H 4e 74
4c S,NTs (1e) H 4f 68 53
5c NTs, NTs (1f) H 4g 79 38
6 O, NTs (1g) CI 4h 84
a

Reactions were performed using 0.4 mmol of 1 and 1.1 equiv of 2a.

b

Isolated yield after chromatography.

c

Reaction performed initially at 90 °C to obtain the mono-Michael adduct; the temperature was then raised to 120 °C for full conversation to the double-Michael product.