Chiral diamides as efficient catalytic precursors for the borane-mediated asymmetric reduction of prochiral ketones

被引：11

作者：

Basavaiah, Deevi ^{[1
]}

Rao, Kalapala Venkateswara ^{[1
]}

Reddy, Bhavanam Sekhara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 08期

关键词：

D O I：

10.1016/j.tetasy.2007.03.034

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral diamides [(2S)-5-oxo-2-(arylamino)carbonylpyrrolidines] derived from the abundantly available (S)-glutamic/(S)-pyroglutamic acids were successfully utilized as effective chiral catalytic precursors in the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene, to provide the corresponding secondary alcohols with up to 91% enantiomeric purities. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：968 / 974

页数：7

共 15 条

[1] Catalytic asymmetric borane reduction of prochiral ketones by the use of chiral β-diamines [J].

Asami, M ;

Sato, S ;

Watanabe, H .

CHEMISTRY LETTERS, 2000, (09) :990-991

[2] A study toward understanding the role of a phosphorus stereogenic center in (5S)-1,3-diaza-2-phospha-2-oxo-3-phenylbicyclo(3.3.0)octane derivatives as catalysts in the borane-mediated asymmetric reduction of prochiral ketones [J].

Basavaiah, D ;

Chandrashekar, V ;

Das, U ;

Reddy, GJ .

TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3955-3962

[3] Toward effective chiral catalysts containing the N-P=O structural framework for the borane-mediated asymmetric reduction of prochiral ketones [J].

Basavaiah, D ;

Reddy, GJ ;

Rao, KV .

TETRAHEDRON-ASYMMETRY, 2004, 15 (12) :1881-1888

[4] A new chiral catalytic source with an N-P=O structural framework containing a proximal hydroxyl group for the borane-mediated asymmetric reduction of prochiral ketones [J].

Basavaiah, D ;

Reddy, GJ ;

Chandrashekar, V .

TETRAHEDRON-ASYMMETRY, 2004, 15 (01) :47-52

[5] (2S,5S)-1,3-Diaza-2-phospha-2-oxo-2-chloro-3-phenylbicyclo[3.3.0] octane:: a novel chiral source for borane-mediated catalytic chiral reductions [J].

Basavaiah, D ;

Reddy, GJ ;

Chandrashekar, V .

TETRAHEDRON-ASYMMETRY, 2002, 13 (11) :1125-1128

[6] A novel and effective chiral phosphoramide catalyst for the borane-mediated asymmetric reduction of prochiral α-halo ketones [J].

Basavaiah, D ;

Reddy, GJ ;

Chandrashekar, V .

TETRAHEDRON-ASYMMETRY, 2001, 12 (04) :685-689

[7] (5S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane:: first example of guanidine based in situ recyclable chiral catalytic source for borane-mediated asymmetric reduction of prochiral ketones [J].

Basavaiah, Deevi ;

Rao, Kalapala Venkateswara ;

Reddy, Bhavanam Sekhara .

TETRAHEDRON-ASYMMETRY, 2006, 17 (07) :1036-1040

[8] (2S)-2-Anilinomethylpyrrolidine:: an efficient in situ recyclable chiral catalytic source for the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene [J].

Basavaiah, Deevi ;

Rao, Kalapala Venkateswara ;

Reddy, Bhavanam Sekhara .

TETRAHEDRON-ASYMMETRY, 2006, 17 (07) :1041-1044

[9] SELECTIVE REDUCTIONS .18. FAST REACTION OF PRIMARY, SECONDARY, AND TERTIARY AMIDES WITH DIBORANE - SIMPLE, CONVENIENT PROCEDURE FOR CONVERSION OF AMIDES TO CORRESPONDING AMINES [J].

BROWN, HC ;

HEIM, P .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (05) :912-916

[10] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

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