Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2006
Problem Set 6: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (10/27/06) from today (10/20/06). Grades will be administered as follows: 5
(exceptional effort), 4 (complete), 3 (incomplete or inadequate effort), 2 (poor effort), 0
(nonexistent). No late problem sets will be accepted.
1. Problem: Trost and Adams have reported the interesting spiroannulation reaction sequence
shown below (JACS, 1983, 105, 4849). In the first step the enolate alkylation produces a single
diastereomeric adduct A. Rearrangement of A under Lewis acid conditions affords a mixture of
B and C. As the reaction times are increased more C is produced by equilibration.