Manganese-Catalyzed Hydrogenation of Sclareolide to Ambradiol

被引：17

作者：

Zubar, Viktoriia ^{[1
]}

Lichtenberger, Niels ^{[1
]}

Schelwies, Mathias ^{[2
]}

Oeser, Thomas ^{[3
]}

Hashmi, A. Stephen K. ^{[1
,3
]}

Schaub, Thomas ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Catalysis Res Lab CaRLa, Neuenheimer Feld 584, D-69120 Heidelberg, Germany

[2] BASF SE, Carl Bosch Str 38, D-67056 Ludwigshafen, Germany

[3] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

CHEMCATCHEM | 2022年 / 14卷 / 01期

关键词：

Sclareolide; Ambrox; manganese; hydrogenation; ester; EFFICIENT;

D O I：

10.1002/cctc.202101443

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The hydrogenation of (+)-Sclareolide to (-)-ambradiol catalyzed by a manganese pincer complex is reported. The hydrogenation reaction is performed with an air- and moisture-stable manganese catalyst and proceeds under relatively mild reaction conditions at low manganese and base loadings. A range of other esters could be successfully hydrogenated leading to the corresponding alcohols in good to quantitative yields using this easy-to-make catalyst. A scale-up experiment was performed leading to 99.3 % of the isolated yield of (-)-Ambradiol.

引用

页数：5

共 28 条

[1]

Allemann, 2002, SYNTHESIS APPL ELECT

[2]

Barrero A.F., 1992, [No title captured], Patent No. [ES2044780 B1, 2044780]

[3]

Barrero A.F., 2011, SYNTHETIC COMMUN, V34, P3631

[4] Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines [J].

Borghs, Jannik C. ;

Lebedev, Yury ;

Rueping, Magnus ;

El-Sepelgy, Osama .

ORGANIC LETTERS, 2019, 21 (01) :70-74

[5] Recent Advances in Nonprecious Metal Catalysis [J].

Buono, Frederic ;

Nguyen, Thach ;

Qu, Bo ;

Wu, Hao ;

Haddad, Nizar .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2021, 25 (07) :1471-1495

[6] Enantioselective Access to (-)-Ambrox® Starting from β-Farnesene [J].

Chapuis, Christian .

HELVETICA CHIMICA ACTA, 2014, 97 (02) :197-214

[7] Dehydrogenative Cross-Coupling of Primary Alcohols To Form Cross-Esters Catalyzed by a Manganese Pincer Complex [J].

Das, Uttam Kumar ;

Ben-David, Yehoshoa ;

Leitus, Gregory ;

Diskin-Posner, Yael ;

Milstein, David .

ACS CATALYSIS, 2019, 9 (01) :479-484

[8] [RuCl2(PPh3)(PNN′)] complexes as efficient catalysts in transfer hydrogenation of ketones [J].

Del Zotto, Alessandro ;

Baratta, Walter ;

Ballico, Maurizio ;

Herdtweck, Eberhardt ;

Rigo, Pierluigi .

ORGANOMETALLICS, 2007, 26 (23) :5636-5642

[9]

Dupau P., 2019, [No title captured], Patent No. [WO 2019/175158A1, 2019175158]

[10] Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes [J].

Elangovan, Saravanakumar ;

Topf, Christoph ;

Fischer, Steffen ;

Jiao, Haijun ;

Spannenberg, Anke ;

Baumann, Wolfgang ;

Ludwig, Ralf ;

Junge, Kathrin ;

Beller, Matthias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) :8809-8814

← 1 2 3 →