A one-pot process for the enantioselective preparation of saturated secondary alcohols from propargyl ketones under hydrogen transfer conditions

被引：12

作者：

Bogliotti, N ^{[1
]}

Dalko, PI ^{[1
]}

Cossy, J ^{[1
]}

机构：

[1] ESPCI, Lab Chim Organ, F-75231 Paris, France

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 40期

关键词：

alcohols; alkynes; asymmetric synthesis; catalysis; hydrogenation; reduction;

D O I：

10.1016/j.tetlet.2005.08.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Propargyl ketones can be directly transformed to enantio-enriched saturated secondary alcohols in a one-pot reaction using chiral RuCI[N-(tosyl)-1,2-diphenylethylenediamine)(p-cymene) and Pd/BaSO4 as catalysts, under transfer hydrogenation conditions. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6915 / 6918

页数：4

共 24 条

[1] Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts
Cossy, J
Bargiggia, F
BouzBouz, S
[J]. ORGANIC LETTERS, 2003, 5 (04) : 459 - 462
[2] Ruthenium-catalyzed asymmetric reduction of 1,3-diketones using transfer hydrogenation
Cossy, J
Eustache, F
Dalko, PI
[J]. TETRAHEDRON LETTERS, 2001, 42 (30) : 5005 - 5007
[3] Synthesis of the C14-C25 subunit of bafilomycin A1
Eustache, F
Dalko, PI
Cossy, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) : 9994 - 10002
[4] Enantioselective monoreduction of 2-alkyl 1,3-diketones using chiral ruthenium catalysts.: Synthesis of the C14-C25 fragment of bafilomycin A1
Eustache, F
Dalko, PI
Cossy, J
[J]. TETRAHEDRON LETTERS, 2003, 44 (49) : 8823 - 8826
[5] Enantioselective monoreduction of 2-alkyl-1,3-diketones mediated by chiral ruthenium catalysts. Dynamic kinetic resolution
Eustache, F
Dalko, PI
Cossy, J
[J]. ORGANIC LETTERS, 2002, 4 (08) : 1263 - 1265
[6] Asymmetric catalytic hydrogenation. Design of new Ru catalysts and chiral ligands: From laboratory to industrial applications
Genet, JP
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (12) : 908 - 918
[7] DIBAL-H-H2NR and DIBAL-H-HNR1R2•HCl complexes for efficient conversion of lactones and esters to amides
Huang, PQ
Zheng, X
Deng, XM
[J]. TETRAHEDRON LETTERS, 2001, 42 (51) : 9039 - 9041
[8] Practical ruthenium/lipase-catalyzed asymmetric transformations of ketones and enol acetates to chiral acetates
Jung, HM
Koh, JH
Kim, MJ
Park, J
[J]. ORGANIC LETTERS, 2000, 2 (16) : 2487 - 2490
[9] QUANTITATIVE EXPRESSION OF DYNAMIC KINETIC RESOLUTION OF CHIRALLY LABILE ENANTIOMERS - STEREOSELECTIVE HYDROGENATION OF 2-SUBSTITUTED 3-OXO CARBOXYLIC ESTERS CATALYZED BY BINAP-RUTHENIUM(II) COMPLEXES
KITAMURA, M
TOKUNAGA, M
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) : 144 - 152
[10] Total synthesis of sulfobacin A through dynamic kinetic resolution of a racemic β-keto-α-amino ester hydrochloride
Labeeuw, O
Phansavath, P
Genêt, JP
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (12) : 1899 - 1908

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