Efficient approaches to the stereoselective synthesis of cyclopropyl alcohols

Accounts of Chemical Research

Volumn 45, Issue 9, 2012, Pages 1533-1547

  Kim, Hun Young ^a   Walsh, Patrick J ^b  

^a INDIANA UNIVERSITY   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; CYCLIZATION; CYCLOPROPANES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84866409871     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar300052s     Document Type: Article

References (64)

1. Salaun, J. Cyclopropane Derivatives and their Diverse Biological Activities Top. Curr. Chem. 2000, 207, 1-67
2. Pellissier, H. Recent Developments in Asymmetric Cyclopropanation Tetrahedron 2008, 64, 7041-7095
3. Pietruszka, J. Synthesis and Properties of Oligocyclopropyl-Containing Natural Products and Model Compounds Chem. Rev. 2003, 103, 1051-1070
4. Wessjohann, L. A.; Brandt, W.; Thiemann, T. Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds Chem. Rev. 2003, 103, 1625-1648
5. Reissig, H.-U.; Zimmer, R. Donor-Acceptor-Substituted Cyclopropane Derivatives and Their Application in Organic Synthesis Chem. Rev. 2003, 103, 1151-1196
6. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Stereoselective Cyclopropanation Reactions Chem. Rev. 2003, 103, 977-1050
7. Rubin, M.; Rubina, M.; Gevorgyan, V. Transition Metal Chemistry of Cyclopropenes and Cyclopropanes Chem. Rev. 2007, 107, 3117-3179
8. Ukaji, Y.; Nishimura, M.; Fujisawa, T. Enantioselective Construction of Cyclopropane Rings via Asymetric Simmons-Smith Reaction of Allylic Alcohols Chem. Lett. 1992, 61-64
9. Charette, A. B.; Prescott, S.; Brochu, C. Improved Procedure for the Synthesis of Enantiomerically Enriched Cyclopropylmethanol Derivatives J. Org. Chem. 1995, 60, 1081-1083
10. Charette, A. B.; Lemay, J. Diastereo- and Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes with Zinc Carbenoids Angew. Chem., Int. Ed. 1997, 36, 1090-1092
11. Charette, A. B.; Molinaro, C.; Brochu, C. Catalytic Asymmetric Cyclopropanation of Allylic Alcohols with Titanium-TADDOLate: Scope of the Cyclopropanation Reaction J. Am. Chem. Soc. 2001, 123, 12168-12175
12. 2- Disulfonamide System Tetrahedron 1995, 51, 12013-12026
13. Balsells, J.; Mejorado, L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Synthesis of Chiral Sulfonamide/Schiff Base Ligands Tetrahedron: Asymmetry 1998, 9, 4135-4142
14. Balsells, J.; Walsh, P. J. Asymmetric Cyclopropanation of Allylic Alcohols Employing Sulfonamide/Schiff Base Ligands J. Org. Chem. 2000, 65, 5005-5008
15. Denmark, S. E.; O'Connor, S. P. Catalytic, Enantioselective Cyclopropanation of Allylic Alcohols. Substrate Generality J. Org. Chem. 1997, 62, 584-594
16. Nugent, W. A. MIB: An Advantageous Alternative to DAIB for the Addition of Organozinc Reagents J. Chem. Soc., Chem. Commun. 1999, 1369-1370
17. Chen, Y. K.; Jeon, S. J.; Walsh, P. J.; Nugent, W. A. Synthesis of (2S)-(-)-3-exo-Morphorlinoisoborneol Org. Synth. 2005, 82, 87-92
18. Kim, H. Y.; Lurain, A. E.; García-García, P.; Carroll, P. J.; Walsh, P. J. Highly Enantio- and Diastereoselective Tandem Generation of Cyclopropyl Alcohols with up to Four Contiguous Stereocenters J. Am. Chem. Soc. 2005, 127, 13138-13139
19. Furukawa, J.; Kawabata, K.; Nishimura, J. A Novel Route to Cyclopropanes from Olefins Tetrahedron Lett. 1966, 28, 3353-3354
20. Lorenz, J. C.; Long, J.; Yang, Z.; Xue, S.; Xie, Y.; Shi, Y. A Novel Class of Tunable Zinc Reagents (RXZnCH2Y) for Efficient Cyclopropanation of Olefins J. Org. Chem. 2004, 69, 327-334
21. Knochel, P.; Vettel, S.; Eisenberg, C. Catalytic Asymmetric Synthesis of Chiral Secondary Polyfunctional Alcohols Using Diorganozincs Appl. Organomet. Chem. 1995, 9, 175-188
22. Charette, A. B.; Lacasse, M.-C. Cyclopropanation of Protected Chiral, Acyclic Allylic Alcohols: Expedient Access to the anti-Cyclopropylcarbinol Derivatives Org. Lett. 2002, 4, 3351-3354
23. Oppolzer, W.; Radinov, R. N. Catalytic Asymmetric Synthesis of Secondary (E)-Allyl Alcohols from Acetylenes and Aldehydes via (1-Alkenyl)zinc Intermediates Helv. Chim. Acta 1992, 75, 170-173
24. Srebnik, M. Stereospecific Preparation of Trisubstituted Allylic Alcohols by Alkene Transfer from Boron to Zinc Tetrahedron Lett. 1991, 32, 2449-2452
25. Kim, H. Y.; Walsh, P. J. Tandem Catalytic Enantio- and Diastereoselective Synthesis of Cyclopropyl Alcohols using Aryl Aldehydes. J. Phys. Org. Chem. 2012, in press.
26. Baldwin, J. E. Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes Chem. Rev. 2003, 103, 1197-1212
27. Davies, H. M. L.; Bruzinski, P. R.; Lake, D.; Kong, N.; Fall, M. Asymmetric Cyclopropanations by Rhodium(II) N-(Arylsulfonyl)prolinate Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Alkenes. Practical Enantioselective Synthesis of the Four Stereoisomers of 2-Phenylcyclopropan-1- amino Acid J. Am. Chem. Soc. 1996, 118, 6897-6907
28. Davies, H. M. L.; Panaro, S. A. Novel Dirhodium Tetraprolinate Catalysts Containing Bridging Prolinate Ligands for Asymmetric Carbenoid Reactions Tetrahedron Lett. 1999, 40, 5287-5290
29. Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. Enantioselective Cyclopropanation of Allylic Alcoholc with Dioxaborolane Ligands: Scope and Synthetic Applications J. Am. Chem. Soc. 1998, 120, 11943-11952
30. Majumdar, S.; de Meijere, A.; Marek, I. Catalytic Asymmetric and Stereoselective Synthesis of Vinylcyclopropanes Synlett 2002, 2002, 0423-0426
31. Kim, H. Y.; Salvi, L.; Carroll, P. J.; Walsh, P. J. One-Pot Catalytic Enantio- and Diastereoselective Syntheses of anti -, syn-cis -Disubstituted, and syn -Vinyl Cyclopropyl Alcohols J. Am. Chem. Soc. 2010, 132, 402-412
32. Miyano, S.; Matsumoto, Y.; Hashimoto, H. Synthesis of Monobromocyclopropanes from Olefins using a Bromocarbenoid of Zinc J. Chem. Soc., Chem. Commun. 1975, 364-365
33. Sugimura, T.; Katagiri, T.; Tai, A. Methyl Carbenoid Addition to Enol Ethers Carrying a Chiral Auxiliary. Stereocontrol of Three Chiral Centers on Cyclopropyl Ether Tetrahedron Lett. 1992, 33, 367-368
34. Fletcher, R. J.; Motherwell, W. B.; Popkin, M. E. The Generation and Trapping of Organozinc Carbenoids from Orthoformates: a Novel Alkoxycyclopropanation Reaction Chem. Commun. 1998, 2191-2192
35. Takai, K.; Toshikawa, S.; Inoue, A.; Kokumai, R. Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and N,N,N',N'-Tetraethylethylenediamine J. Am. Chem. Soc. 2003, 125, 12990-12991
36. Beaulieu, L.-P. B.; Zimmer, L. E.; Charette, A. B. Enantio- and Diastereoselective Iodocyclopropanation of Allylic Alcohols by Using a Substituted Zinc Carbenoid Chem.-Eur. J. 2009, 15, 11829-11832
37. Fournier, J.-F.; Mathieu, S.; Charette, A. B. Diastereoselective Zinco-Cyclopropanation of Chiral Allylic Alcohols with gem-Dizinc Carbenoids J. Am. Chem. Soc. 2005, 127, 13140-13141
38. Marek, I.; Beruben, D.; Normant, J.-F. Metal-Alkene pi-Chelation: A Stereodirecting Effect in Allylzincation Reactions and in Zinc Mediated Cyclopropanations Tetrahedron Lett. 1995, 36, 3695-3698
39. Beruben, D.; Marek, I.; Normant, J. F.; Platzer, N. Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics J. Org. Chem. 1995, 60, 2488-2501
40. 2· (toluene) Organometallics 2006, 25, 3311-3313
41. Knochel, P.; Singer, R. D. Preparation and Reactions of Polyfunctional Organozinc Reagents in Organic Synthesis Chem. Rev. 1993, 93, 2117-2188
42. Kim, H. Y.; Salvi, L.; Carroll, P. J.; Walsh, P. J. Highly Enantio- and Diastereoselective One-Pot Methods for the Synthesis of Halocyclopropyl Alcohols J. Am. Chem. Soc. 2009, 131, 954-962
43. House, H. O.; Fischer, W. F. J. Chemistry of Carbanions. XVII. Addition of Methyl Organometallic Reagents to Cyclohexenone Derivatives J. Org. Chem. 1968, 33, 949-951
44. Hiyama, H.; Yamamoto, H.; Nishio, K.; Kitatani, K.; Nozaki, H. Alkylation of Bromocyclopropanes and Bromoarenes by Means of Dibutylcopperlithium and Alkyl Halides Bull. Chem. Soc. Jpn. 1979, 52, 3632-3637
45. Jeon, S.-J.; Fisher, E. L.; Carroll, P. J.; Walsh, P. J. Direct, Stereospecific Generation of (Z)-Disubstituted Allylic Alcohols J. Am. Chem. Soc. 2006, 128, 9618-9619
46. Campbell, J. B. J.; Molander, G. A. Improved Synthesis of cis -Alkenylboranes J. Organomet. Chem. 1978, 156, 71-79
47. Salvi, L.; Jeon, S.-J.; Fisher, E. L.; Carroll, P. J.; Walsh, P. J. Catalytic Asymmetric Generation of (Z)-Disubstituted Allylic Alcohols J. Am. Chem. Soc. 2007, 129, 16119-16125
48. Salvi, L.; Kim, J. G.; Walsh, P. J. Practical Catalytic Asymmetric Synthesis of Diaryl-, Heteroaryl- and Diheteroarylmethanols J. Am. Chem. Soc. 2009, 131, 12483-12493
49. Davies, H. M. L.; Cantrell, W. R., Jr. α-Hydroxy Esters as Inexpensive Chiral Auxiliaries in Rhodium (II)-Catalyzed Cyclopropanation with Vinyldiazomethanes Tetrahedron Lett. 1991, 32, 6509-6512
50. Hamada, T.; Ye, X.; Stahl, S. S. Copper-Catalyzed Aerobic Oxidative Amidation of Terminal Alkynes: Efficient Synthesis of Ynamides J. Am. Chem. Soc. 2008, 130, 833-835
51. Tsai, C.-C.; Hsieh, I. L.; Cheng, T.-T.; Tsai, P.-K.; Lin, K.-W.; Yan, T.-H. New, General, and Practical Enamine Cyclopropanation Using Dichloromethane Org. Lett. 2006, 8, 2261-2263
52. Song, Z.; Lu, T.; Hsung, R. P.; Al-Rashid, Z. F.; Ko, C.; Tang, Y. Stereoselective Simmons-Smith Cyclopropanation of Chiral Enamides Angew. Chem., Int. Ed. 2007, 46, 4069-4072
53. Valenta, P.; Carroll, P. J.; Walsh, P. J. Stereoselective Synthesis of β-Hydroxy Enamines, Aminocyclopropanes, and 1,3-Amino Alcohols via Asymmetric Catalysis J. Am. Chem. Soc. 2010, 132, 14179-14190
54. 3-Geminated Organodimetallics Chem. Rev. 1996, 96, 3241-3268
55. 2 Geminated Organobismetallic Derivatives Chem. Rev. 2000, 100, 2887-2900
56. Waas, J. R.; Sidduri, A.; Knochel, P. Preparation and Reactions of 1,1-Zinc, Boron and 1,1-Copper, Boron Alkenyl Bimetallics Tetrahedron Lett. 1992, 33, 3717-3720
57. Shimizu, M.; Kurahashi, T.; Kitagawa, H.; Hiyama, T. gem-Silylborylation of an sp Carbon: Novel Synthesis of 1-Boryl-1-silylallenes Org. Lett. 2003, 5, 225-227
58. Deloux, L.; Srebnik, M.; Sabat, M. Stereospecific Synthesis of Temarotene, Its Structural Isomers, and Mixed Triaryl Alkenes from gem-Borazirconocene Alkenes J. Org. Chem. 1995, 60, 3276-3277
59. Li, H.; Carroll, P. J.; Walsh, P. J. Generation and Tandem Reactions of 1-Alkenyl-1,1-Heterobimetallics: Practical and Versatile Reagents for Organic Synthesis J. Am. Chem. Soc. 2008, 130, 3521-3531
60. Kulinkovich, O. G. The Chemistry of Cyclopropanols Chem. Rev. 2003, 103, 2597-2632
61. Hussain, M. M.; Li, H.; Hussain, N.; Ureña, M.; Carroll, P. J.; Walsh, P. J. Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols and 2,3-Disubstituted Cyclobutanones J. Am. Chem. Soc. 2009, 131, 6516-6524
62. Ukai, K.; Oshima, K.; Matsubara, S. Preparation of cyclopropanediol: Novel [2 + 1] cycloaddition reaction of bis(iodozincio)methane with 1,2-diketones. J. Am. Chem. Soc. 2000, 122, 12047-12048.
63. Nomura, K.; Matsubara, S. Preparation of Zinc-Homoenolate from alpha-Sulfonyloxy Ketone and Bis(iodozincio)methane Chem. Lett. 2007, 36, 164-165
64. Cheng, K.; Carroll, P. J.; Walsh, P. J. Diasteroselective Preparation of Cyclopropanols Using Methylene Bis(iodozinc) Org. Lett. 2011, 13, 2346-2349