Antimony(III) chloride catalyzed direct three component one-pot Mannich reaction

Natural Product Communications

Volumn 4, Issue 2, 2009, Pages 247-250

  Shukla, Prashant ^a   Chattopadhyay, Nilmadhab ^a   Nayak, Sandip K ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Antimony(III) chloride; Mannich reaction; One pot; amino ketones

Indexed keywords

ALDEHYDE; ANILINE DERIVATIVE; ANTIMONY DERIVATIVE; KETONE DERIVATIVE; SCHIFF BASE; ANTIMONY; MANNICH BASE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENVIRONMENTAL TEMPERATURE; MANNICH REACTION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMISTRY;

ALDEHYDES; ANTIMONY; CATALYSIS; MANNICH BASES; MOLECULAR STRUCTURE;

EID: 66849142395     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0900400216     Document Type: Article

References (17)

1. Arend M, Westermann B, Risch N. (1998) Modern variants of the Mannich reaction. Angewandte Chemie International Edition, 37, 1044-1070.
2. Corey EJ, Balanson RD. (1974) A total synthesis of (±) porantherine. Journal of the American Chemical Society, 96, 6516-6517.
3. (a) Gracia J, Casamitjana N, Bonjoch J, Bosch J. (1994) Total synthesis of uleine-type and Strychnos alkaloids through a common intermediate. Journal of Organic Chemistry, 59, 3939-3951; (Pubitemid 24248151)
4. (b) Casamitjana N, Gracia J, Bonjoch J, Bosch J. (1992) Studies on the synthesis of Strychnos indole alkaloids. An efficient stereocontrolled synthetic route to 2,4,8- and 2,8,9-trisubstituted 2-azabicyclo[3.3.1]nonan-7-ones. Tetrahedron Letters, 33, 2055-2058;
5. (c) Bonjoch J, Quirante J, Sole D, Castells J, Galceran M, Bosch J. (1991) 8-Aryl-2-azabicyclo[3.3.1]nonan-7-ones. Synthesis and retro Michael ring opening. Tetrahedron, 47, 4417-4428.
6. For catalytic Mannich type reactions, see: (a) Guo QX, Liu H, Guo C, Luo SW, Gu Y, Gong LZ. (2007) Chiral Bronsted acid catalyzed direct asymmetric Mannich reaction. Journal of the American Chemical Society, 129, 3790-3791;
7. (b) Cordova A. (2004) The direct catalytic asymmetric Mannich reaction. Accounts Chemical Research 37, 102-112;
8. (c) Hayashi Y, Tsuboi, W, Shoji M, Suzuki N. (2003) Application of high pressure induced by water freezing to the direct catalytic asymmetric three component List-Barbas-Mannich reaction Journal of the American Chemical Society, 125, 11208-11209; (Pubitemid 37108051)
9. (d) List B, Pojarliev P, Biller WT, Martin HJ. (2002) The proline catalyzed direct asymmetric three component Mannich reaction: Scope, optimization and application to the highly enantioselective synthesis of 1,2-aminoalcohol. Journal of the American Chemical Society, 124, 827-833.
10. (a) Wang R, Li Bg, Huang Tk, Shi L, Lu Xx. (2007) NbCl5 catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds. Tetrahedron Letters, 48, 2071-2073; (Pubitemid 46275873)
11. (b) Ollevier T, Nadeau E, Guay-Bégin AA. (2006) Bismuth triflate catalyzed three component Mannich-type reaction. Tetrahedron Letters, 47, 8351-8354;
12. (c) Ollevier T, Nadeau E. (2004) Bismuth triflate catalyzed three component Mannich type reaction. Journal of Organic Chemistry, 69, 9292-9295;
13. 3-catalyzed reaction of imines with silyl enolates and Diels-Alder reaction of imines. Synlett, 233-234;
14. 2 catalyzed Mannich type reactions of aldehydes, amine and silyl enolates in micellar system. Facile synthesis of β-amino ketones and esters in water. Synlett, 545-546;
15. (f) Makioka Y, Shindo T, Taniguchi Y, Takaki K, Fujiwara Y. (1995) Ytterbium(III) triflate catalyzed synthesis of quinoline derivatives from N-aryl aldimines and vinyl ethers. Synthesis, 801-804.
16. Maiti G, Kundu P. (2006) Imino Diels-Alder reaction: an efficient one-pot synthesis of pyrano and furoquinoline derivatives catalyzed by SbCl3. Tetrahedron Letters, 47, 5733-5736. (Pubitemid 44040893)
17. 2 catalyzed stereoselective synthesis of β-aminoketones via a direct Mannich-type reaction Tetrahedron Letters, 48, 6801-6804.