Pd(0)-Catalyzed Carboiodination: Early Developments and Recent Advances - New Trends in Cross-Coupling: Theory and Applications - page 310

(a)

H I

I

H

H

Me L Pd

Me

Me

R

R R

R

O

PdLn

O Me

O

O

I

I

cis , major

maximized A 1,2 strain

minimized A 1,2 strain

I

I

(b)

PdLn

Me

Me

Me

O

O

O

R

R

PdLn R

Me

I

O R H

I H

H

maximized axial-axial
interactions

trans , major

minimized axial-axial
interactions

Figure 7.3 Stereochemical rationale for the synthesis of (a) isochromans and (b) chromans.

Adapted from Ref. 102. Copyright 2012 American Chemical Society.