ASYMMETRIC CARBON – CARBON BOND- FORMING REACTIONS - Catalytic Asymmetric Synthesis - page 679

Pd(dba) 2 (3 mol %)
159 (6 mol %)
i -Pr 2 NEt (2 eq)

Pd(dba) 2 (3 mol %)
160 (6 mol %)
i -Pr 2 NEt (2 eq)
Toluene, 80°C

ArOTf

Ar + R

N

N

N

Toluene, 80°C

149

CO 2 Me CO 2 Me

CO 2 Me

( S ) -179 ( R ) -179

178

46-48%
60-70% ee

63-83%
87-89% ee

Ar = p -MeO-C 6 H 4 , p -F-C 6 H 4

[Pd 2 (dba) 3 ]•dba (2.5 mol %)
163 (5.6 mol %)
i -Pr 2 NEt (2 eq)

OTf

+

THF, 50°C

181

180

149

76%, 95% ee

(4.0 eq)

Scheme 8C.55.

( 180 ) with 149 using Pd - 163 as the chiral catalyst gave ( R ) - 3 - phenylcyclopent - 1 - ene ( 181 )
in good yield and 95% ee with 94% regioselectivity (Scheme 8C.55) [91].

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