Regioselective Reductive Cross-Coupling Reaction
Regioselective Reductive Cross-Coupling Reaction
Regioselective Reductive Cross-Coupling Reaction
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1.3 Allen<br />
1.3.1 allene+ alkyne<br />
Micalizio et. al. Chem. Commun. 2007, 4531.<br />
OH<br />
Me<br />
•<br />
+<br />
OPMB<br />
PMBO<br />
OH<br />
Me<br />
74%<br />
OPMB<br />
OPMB<br />
alkyne (1.4 eq.), Ti(O i -Pr) 4 (2.1 eq.), c-C 5H 9MgCl (4.2 eq.),<br />
PhMe (-78 ºC to -30 ºC), cool to -78 ºC then add allenyl<br />
alkoxide (1 eq.), (-78 ºC to 0 ºC).<br />
1.3.2 allene+ imine<br />
iPr OH + Cl<br />
•<br />
Micalizio et. al. Synlett, 2008, 735.<br />
nPr N<br />
Cl<br />
n Pr<br />
NH<br />
iPr 63%, E/Z = >20:1<br />
Typical reaction conditions: imine (1.0 equiv), ClTi(Oi-Pr) 3<br />
(1.25 equiv), c-C 5H 9MgCl (2.5 equiv), Et 2O (-78 ºC to -40<br />
ºC), then add allenyl alkoxide (3-4 equiv, -40 ºC to 0 ºC).<br />
Micalizio et. al. Tetrahedron 2008, 68, 3437.<br />
7/16
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