The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

• Shlomo Levinger,
• Ranjeet Nair and
• Alfred Hassner

Beilstein J. Org. Chem. 2008, 4, No. 32, doi:10.3762/bjoc.4.32

• as decisive for the remote transmission of chirality. Keywords: cation–π interaction; conjugate addition; diastereoselectivity; regioselectivity; remote chiral induction; Introduction Recently we have disclosed a pathway for remote asymmetric induction in conjugate additions involving lithiated α

• acetophenones. Preparation of [(9-anthryl)alkyl]- and (mesitylalkyl)amines 6h and 6j from nitriles via imines 8. Preparation of α-sulfonylallylic donor precursors 1 according to Scheme 2. Remote chiral induction in the conjugate addition of lithiated α-sulfonylallyl anions of 1 to ethyl crotonate (2