Enantioselective Rh-catalyzed hydrogenation of enol acetates and enol carbamates with monodentate phosphoramidites

被引：70

作者：

Panella, L

Feringa, BL

de Vries, JG

Minnaard, AJ

机构：

[1] Univ Groningen, Dept Organ & Mol Inorgan Chem, Stratingh Inst, NL-9747 AG Groningen, Netherlands

[2] DSM Res & Patents, Life Sci Adv Synth, Catalysis & Dev, NL-6160 MD Geleen, Netherlands

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 19期

关键词：

D O I：

10.1021/ol051559c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monodentate phosphoramidites, in particular PipPhos and its octahydro analogue, are excellent ligands for the rhodium-catalyzed asymmetric hydrogenation of aromatic enol acetates, enol carbamates, and 2-dienol carbamates up to 98% ee. These latter substrates were hydrogenated selectively to the carbamates of the allyl alcohol.

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页码：4177 / 4180

页数：4

相关论文

共 45 条

[1] CYCLOREVERSIONS OF ANIONS FROM TETRAHYDROFURANS - CONVENIENT SYNTHESIS OF LITHIUM ENOLATES OF ALDEHYDES [J].

BATES, RB ;

POTTER, DE ;

KROPOSKI, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (04) :560-&

[2] PipPhos and MorfPhos: Privileged monodentate phosphoramidite ligands for rhodium-catalyzed asymmetric hydrogenation [J].

Bernsmann, H ;

van den Berg, M ;

Hoen, R ;

Minnaard, AJ ;

Mehler, G ;

Reetz, MT ;

De Vries, JG ;

Feringa, BL .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :943-951

[3] Asymmetric hydrogenation of acyclic enol esters [J].

Boaz, NW .

TETRAHEDRON LETTERS, 1998, 39 (31) :5505-5508

[4]

Brown J. M., 1999, COMPREHENSIVE ASYMME, V1

[5] C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519

[6]

Chaloner P A., 1994, Homogeneous Hydrogenation, DOI [DOI 10.1007/978-94-017-1791-5, 10.1007/978-94-017-1791-5]

[7] Synthesis of novel chiral binaphthyl phosphorus ligands and their applications in Rh-catalyzed asymmetric hydrogenation [J].

Chi, YX ;

Zhang, XM .

TETRAHEDRON LETTERS, 2002, 43 (27) :4849-4852

[8]

Claver C, 2000, CHEM COMMUN, P961

[9]

DEVRIES AHM, 2005, CHIM OGGI, V23, P18

[10] Enantiomerically pure 1,2,5-triphenylphospholane through the synthesis and resolution of the chiral trans-(2,5)-diphenylphospholanic acid [J].

Guillen, F ;

Fiaud, JC .

TETRAHEDRON LETTERS, 1999, 40 (15) :2939-2942

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