1374559-97-3Relevant academic research and scientific papers
Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin
Ren, Xiang,Lu, Zhan
, p. 8370 - 8374 (2021/11/01)
Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral β,β-disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope.
Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols
González-Granda, Sergio,Lavandera, Iván,Gotor-Fernández, Vicente
, p. 13945 - 13951 (2021/04/22)
The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.
The synthesis of non-racemic β-alkyl-β-aryl-disubstituted allyl alcohols and their transformation into allylamines and amino acids bearing a quaternary stereocenter
Narczyk, Aleksandra,Pieczykolan, Micha?,Stecko, Sebastian
supporting information, p. 3921 - 3946 (2018/06/08)
A synthesis of non-racemic β-alkyl-β-aryl allyl alcohols and their transformation into allylamines bearing a quaternary stereogenic center is reported. The allyl alcohols were prepared either by Cu-catalyzed enantioselective reduction of enones or by sequ
A multicomponent Ni-, Zr-, and Cu-catalyzed strategy for enantioselective synthesis of alkenyl-substituted quaternary carbons
McGrath, Kevin P.,Hoveyda, Amir H.
supporting information, p. 1910 - 1914 (2014/03/21)
The availability of enantiomerically enriched carbonyl-containing compounds is essential to the synthesis of biologically active molecules. Since catalytic enantioselective conjugate addition (ECA) reactions directly generate the latter valuable class of molecules, the design and development of such protocols represents a compelling objective in modern chemistry. Herein, we disclose the first solution to the problem of ECA of alkenyl groups to acyclic trisubstituted enones, an advance achieved by adopting an easily modifiable and fully catalytic approach. The requisite alkenylaluminum reagents are synthesized with exceptional site- and/or stereoselectivity by a Ni-catalyzed hydroalumination process, and the necessary enones are prepared through a site- and stereoselective zirconocene-catalyzed carboalumination/acylation reaction. The all-catalytic procedure is complete within four hours, furnishing the desired products in up to 77 % overall yield and 99:1 enantiomeric ratio. One-two-three punch: Ni-catalyzed alkyne hydroalumination, Zr-catalyzed alkyne carbometalation/acylation, and Cu-catalyzed enantioselective conjugate addition are combined for accessing acyclic organic molecules that contain an alkene-substituted quaternary carbon stereogenic center. The entire process takes less than four hours and affords products in up to 77 % overall yield and 99:1 enantiomeric ratio. Copyright
