Abstract
The ruthenium-catalyzed olefin cross-metathesis between pinacol allylboronate, CH2 =CHCH2 B(O2 C2 Me4 ), and RCH=CH2 giving RCH=CHCH2 B(O2 C2 Me4 ) was carried out in refluxing CH2 Cl2 in the presence of an alkylidene-ruthenium complex (3 mol%).
Key words
allylboron - olefin cross-metathesis - ruthenium catalyst
References
1a Hoffmann RW.
Angew. Chem. Int. Ed. Engl.
1982,
21:
555
1b Roush WR. In
Comprephensive Organic Synthesis
Vol. 2:
Heathcock CH.
Pergamon;
Oxford:
1991.
p.1-54
1c Matteson DS.
Stereodirected Synthesis with Organoboranes
Springer;
Berlin:
1995.
2a Rauchschwalbe G.
Schlosser M.
Helv. Chim. Acta.
1975,
58:
1094
2b Matteson DS.
Synthesis
1986,
973
2c Matteson DS.
Tetrahedron
1989,
45:
1859
3a Brown HC.
DeLue NR.
Yamamoto Y.
Maruyama K.
Kasahara T.
Murahashi S.-I.
Sonoda A.
J. Org. Chem.
1977,
42:
4088
3b Wuts PGM.
Thompson PA.
Callen GR.
J. Org. Chem.
1983,
48:
5398
3c Hoffmann RW.
Zeiss H.-J.
J. Org. Chem.
1982,
46:
1309
4a Brümmer O.
Rückert A.
Belchert S.
Chem. Eur. J.
1997,
3:
441
4b Schuster M.
Belchert S.
Angew. Chem. Int. Ed.
1997,
36:
2037
4c Grubbs RH.
Chang S.
Tetahedron
1998,
54:
4413
4d Roy R.
Das SK.
Chem. Commun.
2000,
519
4e Fürstner A.
Angew. Chem. Int. Ed. Engl.
2000,
39:
3013
4f Grubbs RH.
Trnka TM.
Acc. Chem. Res.
2001,
34:
18
5a Crowe WE.
Goldberg DR.
Zhang ZJ.
Tetrahedron Lett.
1996,
37:
2117
5b Engelhardt FC.
Schmitt MJ.
Taylor RE.
Org. Lett.
2001,
3:
2209
6 Feng J.
Schuster M.
Blechert S.
Synlett
1997,
129
7a Renaud J.
Ouellet SG.
J. Am. Chem. Soc.
1998,
120:
7995
7b Renaud J.
Graf C.-D.
Oberer L.
Angew. Chem. Int. Ed.
2000,
39:
3101
8 Choi T.-L.
Chatterjee AK.
Grubbs RH.
Angew. Chem. Int. Ed.
2001,
40:
1277
9a Balckwell HE.
O’Leary DJ.
Chatterjee AK.
Washenfelder RA.
Bussmann DA.
Grubbs RH.
J. Am. Chem. Soc.
2000,
122:
58
9b Sanford MS.
Love JA.
Grubbs RH.
J. Am. Chem. Soc.
2001,
123:
6543
10
16c : HPLC on Chiralcel OB-H (Dicel Co., Ltd) with hexane-2-propanol (99.5:0.5) showed 82% ee; [α]D
25 = +37.5 (c 1.02, CHCl3 ); 1 H NMR (400 MHz, CDCl3 ) δ 5.73 (ddd, 1 H, J = 17.1, 10.2 and 8.3 Hz), 5.11-5.29 (m, 4 H), 3.24 (dddd, 1 H, J = 7.6 Hz), 2.69 (dd, 1 H, J = 17.3 and 8.0 Hz), 2.50 (dd, 1 H, J = 17.3 and 7.6 Hz), 1.78 (s, 1 H), 1.71 (s, 1 H). Two percent of NOE was observed between two hydrogens at the carbon atoms attached to ethenyl and 2-methyl-1-propenyl group; 13 C NMR (100 MHz, CDCl3 ) δ 18.4, 25.8, 34.3, 43.7, 79.7, 117.7, 118.7, 134.3, 140.3, 176.2; exact mass calcd for C10 H14 O2 166.0994, found 166.0992.
