hl - American Chemical Society

hl . . Rz . . . . ;?? OEt. "(i) Ethyl vinyl ether (9 equiv), bromine (6 equiv), methylene chloride, -78 "C 30 min - room temperature 1 h; then 4 in NE...
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3452

J . A m . Chem. SOC.1989, 1 1 1 , 3452-3454

Scheme IIa

6

a

R= H

' Ch

& R-H

h

R= CH(OEt)CH2Br

R=CH,CH,CN

S R=CN ! l R= CH,CH=CH,

.98 and >95%, respectively. Similarly 11 gave >98% pure 12 in 71% yield. Prolonged reaction times must be avoided, since they led to lower stereoselectivity figures. Throughout this investigation, the ste(9) Tour, J. M.; Negishi, E. J . Am. Chem. SOC.1985, 107, 8289.

0 1989 American Chemical Society