ORGN 664 |
| A route has been developed for the synthesis of chiral lactams utilizing a [3+2] annulation reaction involving chiral alpha-siloxy allylsilanes 1 and chlorosulfonyl isocyanate (CSI). Chiral alpha-siloxy allylsilanes are derived from asymmetric reduction of acylsilanes using a chiral lithium amide, affording allylsilanes in high enantiopurity. The subsequent annulation process exhibits a high degree of stereoselectivity affording only lactams 2, in most cases, as one diastereomer. The lactams synthesized using this methodology also possess latent functionality for further synthetic manipulation via N-acyl imminium ion intermediates.
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New Reactions and Methodology
1:00 PM-5:00 PM, Wednesday, 16 March 2005 Convention Center -- Ballroom 20 C-D, Oral
Division of Organic Chemistry |
