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Chem436ProbSetKey8 - #8 Name TA 1 nor excessively elevated...

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Chemistry 436 Problem Set #8 Name:____________________ TA:________________________ 1. ) The following is a derivative of the Fischer Indole Synthesis that requires neither acid nor excessively elevated temperatures to proceed. Please provide a mechanism for this transformation. Miyata et al. Tetrahedron. 1999 (40). 3601-3604 B is another molecule of the starting material. 2.) Please provide reagents for the following transformation. Furthermore provide a mechanism for any rearrangement steps. Kawasaki et al. JOC. 2001 (66). 1200-1204 H N OH H N O N O O Ph 3 P CO 2 Me N O MeO 2 C N O CO 2 Me [Ox] Cl O N N O CF 3 Toluene 90 o C N N N O CF 3 N N O CF 3 B H B-H NH N O CF 3 H-B N HN O CF 3 H N HN O CF 3 H B: N H N OH N O CO 2 Me
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3.) a. The following artificial amino acid, 2,3‐diaminopropionic acid (DAP), is often used to probe the importance of side chain length in the formation of protein secondary structure. Please provide a mechanism for the following transformation. b. If only a single Boc protecting group is used to protect the amine is used DAP is not the product isolated. Please provide the structure of this unexpected product.
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