Stereoselective halocyclization of alkenes with n-acyl hemiaminal nucleophiles

Chirality

Volumn 25, Issue 11, 2013, Pages 805-809

  Liu, Na ^a   Wang, Hao Yuan ^a   Zhang, Wei ^a   Jia, Zhi Hong ^b   Guzei, Ilia A ^a   Xu, Hua Dong ^b   Tang, Weiping ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b CHANGZHOU UNIVERSITY   (China)

Author keywords

alkene; halocyclization; hemiaminal; stereoselective

Indexed keywords

ALKENE DERIVATIVE; CARBON; NUCLEOPHILE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; BROMINATION; COLUMN CHROMATOGRAPHY; CYCLIZATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

ALKENE; HALOCYCLIZATION; HEMIAMINAL; STEREOSELECTIVE;

ALKENES; AMINES; CYCLIZATION; HALOGENS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84886640896     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22219     Document Type: Article

References (58)

1. Harding KE, Tiner TH,. In:, Trost BM, Fleming I, editors. Comprehensive organic synthesis. Vol. 4. Oxford, UK: Pergamon Press; 1991. p 363.
2. Rodriguez J, Dulcere JP,. Cohalogenation in organic-synthesis. Synthesis 1993: 1177-1205.
3. Snyder SA, Treitler DS, Brucks AP,. Halonium-induced cyclization reactions. Aldrichim Acta 2011; 44: 27.
4. Kitagawa O, Taguchi T,. Iodocarbocyclization and iodoaminocyclization reactions mediated by a metallic reagent. Synlett 1999: 1191-1199.
5. Gribble GW,. Naturally occurring organohalogen compounds. Acc Chem Res 1998; 31: 141-152.
6. Gribble GW,. Natural organohalogens: a new frontier for medicinal agents? J Chem Educ 2004; 81: 1441-1449.
7. Vaillancourt FH, Yeh E, Vosburg DA, Garneau-Tsodikova S, Walsh CT,. Nature's inventory of halogenation catalysts: oxidative strategies predominate. Chem Rev 2006; 106: 3364-3378.
8. Wagner C, El Omari M, Konig GM,. Biohalogenation: Nature's way to synthesize halogenated metabolites. J Nat Prod 2009; 72: 540-553.
9. Paul C, Pohnert G,. Production and role of volatile halogenated compounds from marine algae. Nat Prod Rep 2011; 28: 186-195.
10. Sakakura A, Ukai A, Ishihara K,. Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites. Nature 2007; 445: 900-903.
11. Snyder SA, Treitler DS, Brucks AP,. Simple reagents for direct halonium-induced polyene cyclizations. J Am Chem Soc 2010; 132: 14303-14314.
12. Zhou L, Chen J, Tan CK, Yeung Y-Y,. Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts. J Am Chem Soc 2011; 133: 9164-9167.
13. Jaganathan A, Garzan A, Whitehead DC, Staples RJ, Borhan B,. A catalytic asymmetric chlorocyclization of unsaturated amides. Angew Chem Int Ed 2011; 50: 2593-2596.
14. Lozano O, Blessley G, del Campo TM, Thompson AL, Giuffredi GT, Bettati M, Walker M, Borman R, Gouverneur V,. Organocatalyzed enantioselective fluorocyclizations. Angew Chem Int Ed 2011; 50: 8105-8109.
15. Hennecke U, Muller CH, Frohlich R,. Enantioselective haloetherification by asymmetric opening of meso-halonium ions. Org Lett 2011; 13: 860-863.
16. Huang D, Wang H, Xue F, Guan H, Li L, Peng X, Shi Y,. Enantioselective bromocyclization of olefins catalyzed by chiral phosphoric acid. Org Lett 2011; 13: 6350-6353.
17. Rauniyar V, Lackner AD, Hamilton GL, Toste FD,. Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst. Science 2011; 334: 1681-1684.
18. Denmark SE, Burk MT,. Enantioselective bromocycloetherification by Lewis base/chiral Bronsted acid cooperative catalysis. Org Lett 2012; 14: 256-259.
19. Whitehead DC, Yousefi R, Jaganathan A, Borhan B,. An organocatalytic asymmetric chlorolactonization. J Am Chem Soc 2010; 132: 3298 -+.
20. Zhang W, Zheng S, Liu N, Werness JB, Guzei IA, Tang W,. Enantioselective bromolactonization of conjugated (Z)-enynes. J Am Chem Soc 2010; 132: 3664-3665.
21. Zhou L, Tan CK, Jiang X, Chen F, Yeung Y-Y,. Asymmetric bromolactonization using amino-thiocarbamate catalyst. J Am Chem Soc 2010; 132: 15474-15476.
22. Veitch GE, Jacobsen EN,. Tertiary aminourea-catalyzed enantioselective iodolactonization. Angew Chem Int Ed 2010; 49: 7332-7335.
23. Murai K, Matsushita T, Nakamura A, Fukushima S, Shimura M, Fujioka H,. Asymmetric bromolactonization catalyzed by a C-3-symmetric chiral trisimidazoline. Angew Chem Int Ed 2010; 49: 9174-9177.
24. Dobish MC, Johnston JN,. Achiral counterion control of enantioselectivity in a Bronsted acid-catalyzed iodolactonization. J Am Chem Soc 2012; 134: 6068-6071.
25. Tan CK, Zhou L, Yeung Y-Y,. Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids. Org Lett 2011; 13: 2738-2741.
26. Jiang X, Tan CK, Zhou L, Yeung Y-Y,. Enantioselective bromolactonization using an S-Alkyl thiocarbamate catalyst. Angew Chem Int Ed 2012; 51: 7771-7775.
27. Chen J, Zhou L, Tan CK, Yeung Y-Y,. An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids. J Org Chem 2012; 77: 999-1009.
28. Murai K, Nakamura A, Matsushita T, Shimura M, Fujioka H,. C3-symmetric trisimidazoline-catalyzed enantioselective bromolactonization of internal alkenoic acids. Chem Eur J 2012; 18: 8448-8453.
29. Tan CK, Le C, Yeung Y-Y,. Enantioselective bromolactonization of Cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst. Chem Commun 2012; 48: 5793-5795.
30. Paull DH, Fang C, Donald JR, Pansick AD, Martin SF,. Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds. J Am Chem Soc 2012; 134: 11128-11131.
31. Tungen JE, Nolsoe JMJ, Hansen TV,. Asymmetric lodolactonization utilizing chiral squaramides. Org Lett 2012; 14: 5884-5887.
32. Fang C, Paull DH, Hethcox JC, Shugrue CR, Martin SF,. Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst. Org Lett 2012; 14: 6290-6293.
33. Ibrahim H, Togni A,. Enantioselective halogenation reactions. Chem Commun 2004: 1147-1155.
34. Chen GF, Ma SM,. Enantioselective halocyclization reactions for the synthesis of chiral cyclic compounds. Angew Chem Int Ed 2010; 49: 8306-8308.
35. Castellanos A, Fletcher SP,. Current methods for asymmetric halogenation of olefins. Chem Eur J 2011; 17: 5766-5776.
36. Tan CK, Zhou L, Yeung YY,. Organocatalytic enantioselective halolactonizations: strategies of halogen activation. Synlett 2011: 1335-1339.
37. Hennecke U., New catalytic approaches towards the enantioselective halogenation of alkenes. Chem Asian J 2012; 7: 456-465.
38. Denmark SE, Kuester WE, Burk MT,. Catalytic, Asymmetric halofunctionalization of alkenes-a critical perspective. Angew Chem Int Ed 2012; 51: 10938-10953.
39. Cai Y, Liu X, Hui Y, Jiang J, Wang W, Chen W, Lin L, Feng X,. Catalytic asymmetric bromoamination of chalcones: highly efficient synthesis of chiral alpha-bromo-beta-amino ketone derivatives. Angew Chem Int Ed 2010; 49: 6160-6164.
40. Cai Y, Liu X, Jiang J, Chen W, Lin L, Feng X,. Catalytic Asymmetric chloroamination reaction of alpha,beta-unsaturated gamma-keto esters and chalcones. J Am Chem Soc 2011; 133: 5636-5639.
41. Nicolaou KC, Simmons NL, Ying Y, Heretsch PM, Chen JS,. Enantioselective dichlorination of allylic alcohols. J Am Chem Soc 2011; 133: 8134-8137.
42. Zhang W, Liu N, Schienebeck CM, Zhou X, Izhar II, Guzei IA, Tang W,. Enantioselective intermolecular bromoesterification of allylic sulfonamides. Chem Sci 2013; 4: 2652-2656.
43. Tomita F, Takahashi K, Tamaoki T,. Quinocarcin, a novel antitumor antibiotic.3. Mode of action. J Antibiot 1984; 37: 1268-1272.
44. Saito H, Hirata T,. Synthetic approach to quinocarcin. Tetrahedron Lett 1987; 28: 4065-4068.
45. Jadulco R, Edrada RA, Ebel R, Berg A, Schaumann K, Wray V, Steube K, Proksch P,. New communesin derivatives from the fungus Penicillium sp derived from the Mediterranean sponge Axinella verrucosa. J Nat Prod 2004; 67: 78-81.
46. Dalsgaard PW, Blunt JW, Munro MHG, Frisvad JC, Christophersen C,. Communesins G and H, new alkaloids from the psychrotolerant fungus Penicillium rivulum. J Nat Prod 2005; 68: 258-261.
47. Tanaka J, Higa T,. Zampanolide, a new cytotoxic macrolide from a marine sponge. Tetrahedron Lett 1996; 37: 5535-5538.
48. Smith AB, Safonov IG, Corbett RM,. Total synthesis of (+)-zampanolide. J Am Chem Soc 2001; 123: 12426-12427.
49. Kellerjuslen C, Kuhn M, Loosli HR, Petcher TJ, Weber HP, Wartburg AV,. Structure of cyclopeptide antibiotic, Sl-7810-Echinocandin-B. Tetrahedron Lett 1976; 17: 4147-4150.
50. Umezawa H, Kondo S, Iinuma H, Kunimoto S, Ikeda Y, Iwasawa H, Ikeda D, Takeuchi T,. Structure of an anti-tumor antibiotic, spergualin. J Antibiot 1981; 34: 1622-1624.
51. Kondo S, Iwasawa H, Ikeda D, Umeda Y, Ikeda Y, Iinuma H, Umezawa H,. The total synthesis of spergualin, an anti-tumor antibiotic. J Antibiot 1981; 34: 1625-1627.
52. Perry NB, Blunt JW, Munro MHG, Pannell LK,. Mycalamide-a, an antiviral compound from a New-Zealand sponge of the genus Mycale. J Am Chem Soc 1988; 110: 4850-4851.
53. Konishi M, Saito K, Numata K, Tsuno T, Asama K, Tsukiura H, Naito T, Kawaguchi H,. Tallysomycin, a new anti-tumor antibiotic complex related to bleomycin. 2. Structure determination of tallysomycin-a and tallysomycin-b. J Antibiot 1977; 30: 789-805.
54. Sasaki M, Tsuda M, Sekiguchi M, Mikami Y, Kobayashi J,. Perinadine a, a novel tetracyclic alkaloid from marine-derived fungus Penicillium citrinum. Org Lett 2005; 7: 4261-4264.
55. Han B, He Z-Q, Li J-L, Li R, Jiang K, Liu T-Y, Chen Y-C,. Organocatalytic regio- and stereoselective inverse-electron-demand aza-Diels-Alder reaction of alpha,beta-unsaturated aldehydes and N-tosyl-1-aza-1,3-butadienes. Angew Chem Int Ed 2009; 48: 5474-5477.
56. Becker H, Sharpless KB,. A new ligand class for the asymmetric dihydroxylation of olefins. Angew Chem Int Ed 1996; 35: 448-451.
57. Li GG, Chang HT, Sharpless KB,. Catalytic asymmetric aminohydroxylation (Aa) of olefins. Angew Chem Int Ed 1996; 35: 451-454.
58. Jacobsen EN, Marko I, Mungall WS, Schroder G, Sharpless KB,. Asymmetric dihydroxylation via ligand-accelerated catalysis. J Am Chem Soc 1988; 110: 1968-1970.