公开(公告)号：WO2021007141A8

公开(公告)日：2021-01-14

申请号：PCT/US2020/040856

申请日：2020-07-06

Applicant: BASF CORPORATION ,  CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： REISMAN, Sarah ,  ROMBOLA, Michael ,  LADD, Carolyn, L. ,  MCLAUGHLIN, Martin, John ,  ZUEND, Stephan ,  GOETZ, Roland

IPC: C07D401/14 ,  C07B53/00 ,  C07C35/18 ,  C07B2200/07 ,  C07C201/12 ,  C07C2601/16 ,  C07C2602/44 ,  C07C2603/74 ,  C07C67/293

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.

公开(公告)号：WO2021007141A1

公开(公告)日：2021-01-14

申请号：PCT/US2020/040856

申请日：2020-07-06

Applicant: BASF CORPORATION ,  CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： REISMAN, Sarah ,  ROMBOLA, Michael ,  LADD, Carolyn, L. ,  MCLAUGHLIN, Martin, John ,  ZUEND, Stephan ,  GOETZ, Roland

IPC: C07D401/14 ,  C07B53/00 ,  C07C35/18

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 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation M m+ 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 R 10a , R 10b , R 10c , R 10d , R 10a' , R 10b' , R 10c' , R 10d' , Z and Z' have the meanings as defined in the description.

公开(公告)号：WO2020010055A1

公开(公告)日：2020-01-09

申请号：PCT/US2019/040254

申请日：2019-07-02

Applicant: BASF SE ,  BASF CORPORATION ,  THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

Inventor： ERNST, Martin ,  ZUEND, Stephan ,  SU, Bo ,  BUNESCU, Ala ,  HARTWIG, John F.

IPC: C07C213/02 ,  C07C249/02 ,  C07C215/08 ,  C07C251/24

Abstract: A process for the preparation of amino alcohols includes condensing a compound of Formula (II), a stereoisomer, a tautomer, or a salt thereof with a compound of Formula (IlIa) or Formula (Illb), a stereoisomer, a tautomer, or a salt thereof to form a condensation product; hydroxylating or acyloxylating the condensation product in the presence of an oxidant to obtain a hydroxylation or acyloxylation product; and subjecting the hydroxylation or acyloxylation product to one or more subsequent reactions comprising a hydrolysis reaction, alcohol deprotection, an amino lysis reaction, or a combination of two or more thereof to obtain an amino alcohol of Formula (I).