Towards chiral diamines as chiral catalytic precursors for the borane-mediated enantioselective reduction of prochiral ketones

被引:4
作者
Basavaiah, Deevi [1 ]
Das, Utpal [1 ]
Roy, Suparna [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
(3S)-3-Anilinomethyl-1,2,3,4-tetrahydroisoquinoline; (2R)-2-anilinomethylpiperidine; (S)-phenylalanine; asymmetric reduction; P=O STRUCTURAL FRAMEWORK; ASYMMETRIC REDUCTION; ANALOGS;
D O I
10.1007/s12039-009-0112-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two chiral diamines (3S)-3-anilinomethyl-1,2,3,4-tetrahydroisoquinoline (1) and (2R)-2-anilinomethylpiperidine (2) have been employed as chiral catalytic sources in the borane-mediated asymmetric reduction of prochiral ketones thus providing the resulting secondary alcohols in good enantiomeric purities (up to 81% ee).
引用
收藏
页码:1003 / 1010
页数:8
相关论文
共 33 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]   Synthesis and opioid activity of N,N-dimethyl-Dmt-Tic-NH-CH(R)-R′ analogues:: Acquisition of potent δ antagonism [J].
Balboni, G ;
Salvadori, S ;
Guerrini, R ;
Negri, L ;
Giannini, E ;
Bryant, SD ;
Jinsmaa, Y ;
Lazarus, LH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (24) :5435-5441
[3]   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
[4]   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
[5]   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
[6]   (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
[7]   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
[8]   Chiral diamides as efficient catalytic precursors for the borane-mediated asymmetric reduction of prochiral ketones [J].
Basavaiah, Deevi ;
Rao, Kalapala Venkateswara ;
Reddy, Bhavanam Sekhara .
TETRAHEDRON-ASYMMETRY, 2007, 18 (08) :968-974
[9]   (5S)-1-aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane:: a novel chiral catalytic source containing the N-(C=NH)-O moiety for the borane-mediated asymmetric reduction of prochiral ketones [J].
Basavaiah, Deevi ;
Rao, Kalapala Venkateswara ;
Reddy, Bhavanam Sekhara .
TETRAHEDRON-ASYMMETRY, 2007, 18 (08) :963-967
[10]   (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