Date of Award

2010

Publisher

North Dakota State University

Document Type

Thesis

Degree Awarded

Master of Science (MS)

Program

Chemistry and Biochemistry

Department

Chemistry and Biochemistry

College

Science and Mathematics

Faculty Advisor

Sibi, Mukund P.

Description

There has been a need in agriculture, medicine, and organic chemistry for enantiopure isoxazolines. A direct method for their synthesis is from the cycloaddition of 1,3-dipoles and alkynes. Alkynones are difficult substrates to use in cycloadditions due to their high reactivity and sometimes instability. Due to their high reactivity it is often difficult to control regio- endo/exo, and enantioselectivities in dipolar cycloadditions of alkynones. This thesis details the cycloadditions of nitrones and alkynones using chiral Lewis acids leading to isoxazolines with high regio-and enantiocontrol. A chiral bisoxazoline-zinc(II) complex successfully catalyzed the enantioselective 1,3-dipolar cycloaddition reaction of nitrone and alkynone derivatives. This is the second successful reported method for the catalytic enantioselective 1,3- dipolar cycloaddition of nitrones and alkynone derivatives. Yields for the cycloadducts were good to near quantitative and enantioselectivities were generally good reaching a high of 86 % ee. The 4-isoxazolines were isolated as single reg101somers.

Rights

NDSU policy 190.6.2

Rights Link

https://www.ndsu.edu/fileadmin/policy/190.pdf

Handle Identifier

https://hdl.handle.net/10365/33753

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