Synthesis of naphthalenes from ortho-substituted benzyl sulfones and michael acceptors
β Scribed by Jurjen Wildeman; Peder C. Borgen; Henk Pluim; Peter H.F.M. Rouwette; Albert M. van Leusen
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 245 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
A communication on a closely related subject by Hauser and RheeI prompt us to disclose our preliminary results on a simple synthetic method for the transformation of benzene derivatives to naphthslenering systems. This novel method' is based on the reaction of ortho-substituted benzyl sulfones (A) with Michael acceptors, followed by elimination of water and p-toluenesulfinic acid (TosH), e.g. Scheme 1.
π SIMILAR VOLUMES
## Abstract A general and efficient method to prepare monoβ and disubstituted divinyl sulfones is reported.
The aza-Michael addition of enantiopure 1-aminopyrrolidines to (E)-alkenyl sulfones in the presence of a catalytic amount of ytterbium trifluoromethanesulfonate [Yb(OTf) 3 ] yields Ξ²-hydrazino sulfones in moderate to good yields and with diastereoselectivities of up to 98%. The latter undergo reduct