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. Author manuscript; available in PMC: 2011 Feb 1.
Published in final edited form as: Nat Chem. 2010 May 23;2(8):638–643. doi: 10.1038/nchem.665

Table 1.

graphic file with name nihms194500t1.jpg
entry allylic alcohol
or
diazoacetate
starting material		 vinylcyclopropane Presumed
metallacyclic intermediatea 		Yield
(%)b 		(E:Z)c drc productd
1 graphic file with name nihms194500t2.jpg graphic file with name nihms194500t3.jpg graphic file with name nihms194500t4.jpg 58
(82% brsm)		 20:1 – graphic file with name nihms194500t5.jpg
2 graphic file with name nihms194500t6.jpg graphic file with name nihms194500t7.jpg graphic file with name nihms194500t8.jpg 54 20:1 – graphic file with name nihms194500t9.jpg
3 graphic file with name nihms194500t10.jpg graphic file with name nihms194500t11.jpg graphic file with name nihms194500t12.jpg 50 20:1 – graphic file with name nihms194500t13.jpg
4 graphic file with name nihms194500t14.jpg graphic file with name nihms194500t15.jpg graphic file with name nihms194500t16.jpg 61 10:1 – graphic file with name nihms194500t17.jpg
5 graphic file with name nihms194500t18.jpg graphic file with name nihms194500t19.jpg graphic file with name nihms194500t20.jpg 55 20:1 20:1 graphic file with name nihms194500t21.jpg
6 graphic file with name nihms194500t22.jpg graphic file with name nihms194500t23.jpg graphic file with name nihms194500t24.jpg 52 20:1 20:1 graphic file with name nihms194500t25.jpg
7 graphic file with name nihms194500t26.jpg graphic file with name nihms194500t27.jpg graphic file with name nihms194500t28.jpg 52 20:1 20:1 graphic file with name nihms194500t29.jpg
8 29 graphic file with name nihms194500t30.jpg graphic file with name nihms194500t31.jpg 42 20:1 20:1 graphic file with name nihms194500t32.jpg
a

Inline graphic = bonds formed in the coupling process.

b

While not computed for examples 2–8, as seen in entry 1, these reactions did not consume all of the vinylcyclopropane starting material.

c

No evidence was found for the production of stereoisomeric products.

d

Reaction conditions for cross-coupling: vinylsilane, ClTi(Oi-Pr)3, c-C5H9MgCl, Et2O (−78 to −50 °C), then add Li-alkoxide of vinylcyclopropane (−70 °C to rt over 3 h).

e

Oxidation conditions: TBHP, H2O, CsOH•H2O, TBAF, DMF, 70 °C.

f

Oxidation conditions: KF, KHCO3, H2O2, MeOH, THF.

g

ICH2Cl, Sm[Hg], THF, (85%, dr ≥ 20:1).

h

PDC, 4 Å sieves, CH2Cl2 (91%), then L-Selectride, THF (76% of desired isomer, dr = 6:1).