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I. Palladium (0)-Catalyzed Asymmetric Rearrangement Of Allyl Enol Ether For The Synthesis Of Α -Aryl Quaternary Carbon Center. Ii. Synthesis Of Chiral Tryptophan Analogs And Studies Towards Synthesis Of Tryprostatin A And B, Md Nazim Uddin

Theses and Dissertations

The development of efficient catalytic enantioselective synthesis of all carbon quaternary centers is a significant challenge in chemical synthesis due to the difficulties of carbon-carbon bond formation at quaternary center. Using phase transfer catalyst we attempted to create quaternary carbon center via direct C-alkylation of hydroxyarylacrylates, instead we obtained O-alkylated acrylates. We succeeded in C-alkylation which involves an indirect method via the O-alkylation of 3-hydroxy aryl acrylates and a subsequent [3, 3] sigmatropic rearrangement (Claisen rearrangement). The O-alkylated products are obtained in yields ranging from 65-85%, and the corresponding Claisen rearrangement products in yields ranging from 55-90%. Typically Pd(II) catalysts …