Patent number: 11926589
Abstract: This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation Mm+ wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R10a, R10b, R10c, R10d, R10a?, R10b?, R10c?, R10d?, Z and Z? have the meanings as defined in the description.
Type:
Grant
Filed:
July 6, 2020
Date of Patent:
March 12, 2024
Assignees:
BASF CORPORATION, CALIFORNIA INSTITUTE OF TECHNOLOGY
Inventors:
Sarah Reisman, Michael Rombola, Carolyn L. Ladd, Martin John McLaughlin, Stephan Zuend, Roland Goetz
Publication number: 20220267247
Abstract: This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation Mm+ wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R10a, R10b, R10c, R10d, R10a?, R10b?, R10c?, R10d?, Z and Z? have the meanings as defined in the description.
Type:
Application
Filed:
July 6, 2020
Publication date:
August 25, 2022
Inventors:
Sarah Reisman, Michael Rombola, Carolyn L. Ladd, Martin John McLaughlin, Stephen Zuend, Roland Goetz
Patent number: 10757938
Abstract: The present invention relates to N-acylimino compound of formula (I): wherein X is O or S, in particular O; m is an integer selected from 0, 1, 2, 3, 4, 5 or 6; Het is a 5 or 6 membered carbon-bound or nitrogen-bound heterocyclic ring, W1-W2-W3-W4 represents a carbon chain group connected to N and C?N, and thus forming a saturated, unsaturated, or partially unsaturated 5 or 6 membered nitrogen containing heterocycle, wherein W1, W2, W3 and W4 each individually represent CRvRw, R1, R2 may be hydrogen, halogen, etc. R3 may be hydrogen, halogen, CN, C1-C6-alkyl, etc. R4a, R4b if present, may be hydrogen, halogen, C1-C6-alkyl, etc. R5 may be hydrogen, halogen, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkinyl, C3-C8-cycloalkyl, S(O)nNR9aR9b, NR9aR9b, C(?O)OR8, C(?O)NR9aR9b, C(?S)NR9aR9b, C(?O)R7a, C(?S)R7a, NR9a—C(?O)R7a, NR9a—C(?S)R7a, NR9a—S(O)nR8a, a moitey Q-phenyl, where the phenyl ring is optionally substituted with one or more, e.g.
Type:
Grant
Filed:
January 11, 2019
Date of Patent:
September 1, 2020
Assignee:
BASF SE
Inventors:
Martin John McLaughlin, Nina Gertrud Bandur, Matthias Pohlman, Jochen Dietz, Wolfgang Von Deyn