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1.
J Org Chem ; 88(22): 15726-15738, 2023 Nov 17.
Article in English | MEDLINE | ID: mdl-37921031

ABSTRACT

A Rh-catalyzed highly chemo- and enantioselective hydrogenation of 2-CF3-chromen/thiochromen-4-ones was successfully established achieving excellent selectivity and high turnover numbers. Under mild conditions, a series of 2-CF3-chromen-4-ones were hydrogenated to provide the corresponding chiral 2-CF3-chroman-4-ones with excellent enantioselectivities (up to 99.9% ee) and achieve high turnover numbers (TON of up to 11,800). Moreover, the obtained hydrogenation products were also successfully transformed into other derivatives including the important intermediate of plasmepsin inhibitors with maintained enantiopurity.

2.
Chem Sci ; 14(34): 9048-9054, 2023 Aug 30.
Article in English | MEDLINE | ID: mdl-37655036

ABSTRACT

A highly enantioselective rhodium-catalyzed reductive dearomatization of 7-substituted pyrazolo[1,5-a]pyrimidines has been realized for the first time by two strategies to afford chiral 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidines with excellent enantioselectivities of up to 98% ee. This method also provides an efficient approach for the synthesis of the powerful BTK inhibitor, zanubrutinib.

3.
Org Lett ; 25(20): 3644-3648, 2023 May 26.
Article in English | MEDLINE | ID: mdl-37184220

ABSTRACT

An efficient Ni-(S,S)-Ph-BPE complex that catalyzed asymmetric hydrogenation of cyclic N-acyl hydrazones has been developed to produce various chiral cyclic hydrazines in high yields with excellent enantioselectivities of up to >99% enantiomeric excess. Moreover, the hydrogenation can not only proceed smoothly on a gram scale under lower catalyst loading (S/C = 3000) without any decrease of enantioselectivity but can also be applied to the asymmetric synthesis of a RIP-1 kinase inhibitor.

4.
Org Lett ; 24(14): 2722-2727, 2022 04 15.
Article in English | MEDLINE | ID: mdl-35363497

ABSTRACT

A highly efficient asymmetric hydrogenation of a series of γ-keto acid derivatives, including γ-keto acids, esters, and amides, using a Ni-(R,R)-QuinoxP* complex as the catalyst has been developed to afford chiral γ-hydroxy acid derivatives with excellent enantioselectivities, up to 99.9% ee. This method provides not only an economical one-pot approach for the synthesis of chiral γ-lactones but also access to (S)-norfluoxetine, an inhibitor of neural serotonin reuptake and an essential intermediate for pharmaceutical synthesis.


Subject(s)
Amides , Esters , Catalysis , Hydrogenation , Hydroxy Acids , Keto Acids , Lactones , Nickel , Stereoisomerism
5.
J Org Chem ; 86(17): 12034-12045, 2021 Sep 03.
Article in English | MEDLINE | ID: mdl-34346217

ABSTRACT

The first asymmetric hydrogenation of ß,ß-diaryl unsaturated phosphonates has been realized for synthesis of ß,ß-diaryl chiral phosphonates with excellent enantioselectivities (up to 99.9% ee) catalyzed by the Rh-(R,R)-f-spiroPhos complex. Furthermore, this catalyst also exhibits comparably excellent performance for ß-aryl-ß-alkyl unsaturated phosphonates providing the corresponding chiral phosphonates with up to 99.9% ee values. This methodology provides a straightforward access to asymmetric synthesis of chiral phosphonates.

6.
Org Lett ; 23(15): 5734-5738, 2021 08 06.
Article in English | MEDLINE | ID: mdl-34240880

ABSTRACT

An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.

7.
Org Biomol Chem ; 15(6): 1407-1417, 2017 Feb 07.
Article in English | MEDLINE | ID: mdl-28101540

ABSTRACT

An asymmetric aldol-desymmetrization sequence was developed which provided highly efficient access to important bicyclic oxygen-containing scaffolds with multiple chiral centers and one is a quaternary stereogenic center containing a free hydroxy group. Moreover, starting from racemic precursors, the final products were obtained as two separable diastereomers by flash chromatography. Several other heterocycles could also be easily generated with this strategy.

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