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Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2006
Problem Set 9: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (11/24/06) from today (11/17/06). 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: The stereoselective metalloenamine alkylation has previously been reported by both
Meyers (JACS, 1976, 98, 3032) and Whitesell (JOC, 1977, 42, 377). Given the stereostructure
of the product, rationalize the stereochemical outcome. In your analysis you should
acknowledge the fact the imine geometry in the product is syn to the newly formed bond.
N
OMe
R
EtMgI
R'-I
N
OMe
R
R'
R = Et (Whitesell); R = Bn (Meyers); Stereoselection >90:10
2. Problem: West provided several examples of a one-flask annulation reaction that provides
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