The Diels-Alder Reaction

OIL

OIL

WATER

O/W

B

W/O

H

CO2Et

sc-H2O

+

CO2Et +

H

375 C

R1

R2

R2

R

1

H

CO2Et

R1

R2

R1

R2

t (h)

endo /exo

Yield (%)

CO2Et

H

1

−

10

H

CO2Et

1

50:50

86

H

H

2

50:50

80

CO2Et

CN

CO2Et

CN

H2O EtO2C

H2O

CO2Et

R1 = Me, R2 = H

R1 = R2 = H

337 C, 1 h, 84%

303 C, 0.5 h, 88%

R1

O

R2

O

CN

H

CN

H2O

H2O O

R1 = R2 = Me

R1 = R2 = Me

293 C, 25 min, 100%

310 C, 0.5 h, 86%

H

O

! "

O

O

sc-CO2

R*

O

+

R*

+

*R

R*

O

(-)

*R

O

*R O

(2R, 3R)

(2S, 3S)

R* =

N

S O

O

O

N

n

R

1

NH

Cl

H

O, 25 C

R1

+

3

2

n

2−120 h, 77−99%

R2

R2

H

O

O