Self-induced diastereoselective oxidation of vinyl sulfoxides bearing a

J. Org. Chem., Vol. 54,No. 13, 1989

Additions and Corrections

3245

A d d it ions and Correct ions Vol. 51, 1986

Ottorino De Lucchi,* Vittorio Lucchini,* Carla Marchioro, Giovanni Valle, and Giorgio Modena. Self-Induced Diastereoselective Oxidation of Vinyl Sulfides Bearing a Chiral Hydroxy Group as a Way of Preparation of Optically Active Sulfinyl Dienophiles and Their Use in the Asymmetric Diels-Alder Reaction to Cyclopentadiene. Page 1457. Structure 4 , 5 , and 11 in Schemes I1 and I11 and structures 13a and 14 in eq 3 have been drawn in the sulfur S

absolute configuration instead of the correct R one. Scheme I has been incorrectly drawn and should be replaced with the new Scheme I. The NOE experiments suggest that the sulfur lone pair and the double bond of the dienophilea 4b,c and 5b,c are syn coplanar. Therefore, the structure of the adducts, as determined by X-ray analysis, are consistent with the attack of cyclopentadiene from the side of the oxygen atom. The arrows in Figures 4 and 5 denote the face on which the addition does not occur. We thank Prof. W. Oppolzer (Gengve) for bringing these points to our attention.

-

Scheme Io

bonds aboveand 4 below (he plane of (he paper

B

fC

+

?OH

1

2

3 major palh

I S Y ~

I

mlnor palh

4 anti

anti

7

I

I

I

\ S02R'

9 10

'a, X = PhS02;b, X = p-C1PhS02; c, X = MeCOO.