[reaction--see text] Enolates of a new camphor-derived lactam auxiliary are shown to monoalkylate with very high diastereoselectivity. A second alkylation occurs with reactive alkylating agents to afford quaternary centers also with high diastereoselectivity. In accord with a proposed model for diastereoselection, lithium and sodium enolates provide products with an opposite sense of asymmetric induction.

No abstract

Toward the Development of a General Chiral Auxiliary. Part 9. Highly Diastereoselective Alkylations and Acylations to Form Tertiary and Quaternary Centers.-Enolates containing a new camphor-derived lactam auxiliary can be alkylated and acylated with good to very high diastereoselectivity. In the case of imides (I) and (III) lithium and sodium enolates leads to products with opposite sense of asymmetric induction. -(BOECKMAN JR., ROBERT K.; BOEHMLER, DEBRA J.; MUSSELMAN, RHONDA A.; Org.

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