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US 2020/0047169 A1Published application
Catalysts for olefin isomerization
AssigneeBrandeis University
InventorsXIAO ZHOU, YONGWEI WU, LI DENG
Life of this patent
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Abstract
Provided herein are cinchonium betaine catalysts and methods of promoting asymmetric butenolide isomerization reactions using the same.
Claims27
A compound, or a salt, tautomer, enantiomer or diastereoisomer thereof, of formula (I):
- wherein X is selected from N and N+—O−;
- R1 is selected from hydrogen, C1-C6 alkoxy, C1-C6 alkyl siloxy, or halogen;
- R2 and R3 are independently selected from hydrogen, C1-C6 alkyl, or alkylsilyl;
- R4 is C1-C6 alkyl or C2-C7 alkenyl;
- R5 is —OH, —O−, or C1-C6 alkoxy;
- R6 is an optionally substituted C5-C6 heteroaryl, wherein each optional substituent is independently selected from aryl and halo, and said C5-C6 heteroaryl may comprise one or more substituents in the carbon ring selected from O, N, and/or S;
- and
- R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, or C1-C6 alkenyl;
- and R3 and R7 may together form a five- or six-membered optionally aromatic fused ring;
- and R2 and R8 may together form a five- or six-membered optionally aromatic fused ring.
7 more elements
A compound having the structure:
A method of promoting lactone isomerization that comprises contacting a lactone having the structure of formula (II):
- wherein Ra, Rb, Rc and Rd are independently selected from hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted alkenyl, where each optional substituent is independently selected from hydroxy, alkyl, alkoxy, and halo;
- and Ra and Rb may together form a fused 5- or 6-membered ring;
- with at least one compound having the structure of the formula (I)
- the structure of formula (I):
- wherein X is selected from N and N+—O−;
- R1 is selected from hydrogen, C1-C6 alkoxy, C1-C6 alkyl siloxy, or halogen;
- R2 and R3 are independently selected from hydrogen, C1-C6 alkyl, or alkylsilyl;
- R4 is C1-C6 alkyl or C2-C7 alkenyl;
- R5 is hydrogen, —OH, —O−, or C1-C6 alkoxy;
- R6 is an optionally substituted C5-C6 heteroaryl, wherein each optional substituent is independently selected from aryl and halo, and said C5-C6 heteroaryl may comprise one or more substituents in the carbon ring selected from O, N, and/or S;
- and
- R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, or C1-C6 alkenyl;
- and R3 and R7 may together form a five or six membered optionally aromatic fused ring;
- and R2 and R8 may together form a five or six membered optionally aromatic fused ring.
- to afford a compound a compound having the structure of formula (III)
12 more elements
Dependencies are inferred from the claim text.