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. Author manuscript; available in PMC: 2012 Nov 11.
Published in final edited form as: Tetrahedron. 2011 Nov 11;67(45):8607–8614. doi: 10.1016/j.tet.2011.09.036

Table 2.

Method Ca: optimal conditions (% isolated yields)

Entry Carbonyl Fulvene (%)
a graphic file with name nihms328210t1.jpg graphic file with name nihms328210t2.jpg 98
b graphic file with name nihms328210t3.jpg graphic file with name nihms328210t4.jpg 97
c graphic file with name nihms328210t5.jpg graphic file with name nihms328210t6.jpg 98
eb graphic file with name nihms328210t7.jpg graphic file with name nihms328210t8.jpg 95
f graphic file with name nihms328210t9.jpg graphic file with name nihms328210t10.jpg 98
gb graphic file with name nihms328210t11.jpg graphic file with name nihms328210t12.jpg 97
hb graphic file with name nihms328210t13.jpg graphic file with name nihms328210t14.jpg 86
kb graphic file with name nihms328210t15.jpg graphic file with name nihms328210t16.jpg 77
le graphic file with name nihms328210t17.jpg graphic file with name nihms328210t18.jpg 11
nb graphic file with name nihms328210t19.jpg graphic file with name nihms328210t20.jpg 90
ob CH3CHO graphic file with name nihms328210t21.jpg 90
pb graphic file with name nihms328210t22.jpg graphic file with name nihms328210t23.jpg 85
qb graphic file with name nihms328210t24.jpg graphic file with name nihms328210t25.jpg 92
rb graphic file with name nihms328210t26.jpg graphic file with name nihms328210t27.jpg 95
sb,c graphic file with name nihms328210t28.jpg graphic file with name nihms328210t29.jpg 44
vb,d graphic file with name nihms328210t30.jpg graphic file with name nihms328210t31.jpg 60
w graphic file with name nihms328210t32.jpg graphic file with name nihms328210t33.jpg 25
x graphic file with name nihms328210t34.jpg graphic file with name nihms328210t35.jpg 30
a

Method C: same as B, no molecular sieves, 5 mL MeOH-H2O (4:1).

b

To a solution of 1o (20 mmol) and CP (10.0 mmol), in MeOH-H2O (10 mL 7/3) pyrrolidine (10 mol%,) was added, and the reaction mixture stirred for 2.5 h at 15 °C. The mixture was poured into an ice-cold mixture of brine solution (10 mL) containing AcOH (1 mmol). The upper oil phase was separated and dried over molecular sieves.

c

To a solution of 2s (5 mmol) and CP (10 mmol) in 5 mL of methanol-water (4:1), pyrrolidine (10 mmol, 2 equiv) was added, and the mixture stirred at room temperature overnight. The mixture was subjected to flash chromatography on silica gel to give 3s in 44% yield.

d

Due to anticipated greater water solubility of product, extractive workup was used.

e

3equiv of pyrrolidine was used: reaction time 24 h.