Computational prediction of the regio- and diastereoselectivity in a rhodium-catalyzed hydroformylation/cyclization domino process

Journal of Molecular Modeling

Volumn 13, Issue 6-7, 2007, Pages 823-837

  Alagona, Giuliano ^a   Ghio, Caterina ^a   Rocchiccioli, Silvia ^b  

^a CNR   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

Annulation; B3LYP 6 31G*; LANL2DZ; Substrate induced diastereoselectivity

Indexed keywords

2 METHYL 3 (3 ACETYLPYRROL 1 YL)PROP 1 ENE; ALDEHYDE DERIVATIVE; PROTON; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; CYCLIZATION; DIASTEREOISOMER; HYDROFORMYLATION; MOLECULAR MODEL; PREDICTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALDEHYDES; ALKENES; CARBON; CATALYSIS; CYCLIZATION; HYDROGEN BONDING; MODELS, MOLECULAR; PROTONS; RHODIUM; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 34347375507     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-007-0205-8     Document Type: Article

References (42)

1. Anh NT, Eisenstein O (1977) Nouv J Chim 1:61-70, (references therein)
2. Eliel EL, Wilen SH, Mander LN (1994) Stereochemistry of organic compounds. Wiley, New York, pp 875-886
3. Houk KN (2000) Theor Chem Acc 103:330-331
4. Torrent M, Solà M, Frenking G (2000) Chem Rev 100:439-493 (references therein)
5. Koga N, Jin SQ, Morokuma K (1988) J Am Chem Soc 110:3417-3425
6. Matsubara T, Koga N, Ding Y, Musaev DG, Morokuma K (1997) Organometallics 16:1065-1078
7. Gleich D, Hutter J (2004) Chem Eur J 10:2435-2444
8. Rocha WR, De Almeida WB (2000) Int J Quantum Chem 78:42-51
9. Gleich D, Schmid R, Herrmann WA (1998) Organometallics 17:4828-4834
10. Carbó JJ, Maseras F, Bo C, van Leeuwen PWNM (2001) J Am Chem Soc 123:7630-7637
11. Alagona G, Ghio C, Lazzaroni R, Settambolo R (2001) Organometallics 20:5394-5404
12. Alagona G, Ghio C, Lazzaroni R, Settambolo R (2004) Inorg Chim Acta 357:2980-2988
13. Alagona G, Ghio C (2005) J Organomet Chem 690:2339-2350
14. Settambolo R, Rocchiccioli S, Lazzaroni R, Alagona G (2006) Lett Org Chem 3:10-12
15. Matsui Y, Orchin M (1983) J Organomet Chem 246:57-60
16. Amer I, Alper H (1990) J Am Chem Soc 112:3674-3676
17. Botteghi C, Cazzolato L, Marchetti M, Paganelli S (1995) J Org Chem 60:6612-6615
18. Lazzaroni R, Settambolo R, Uccello-Barretta G, Caiazzo A, Scamuzzi S (1999) J Mol Cat A Chemical 143:123-130
19. Lazzaroni R, Settambolo R, Caiazzo A, Pontorno L (2000) J Organomet Chem 601:320-323
20. Settambolo R, Caiazzo A, Lazzaroni R (2001) Tetrahedron Lett 42:4045-4048
21. Gaussian 03, Revision C.02: Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian H. P, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian Inc. Wallingford CT
22. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785-789
23. Becke AD (1993) J Chem Phys 98:5648-5652
24. Hehre WJ, Radom L, Schleyer PvR, Pople JA (1986) Ab initio molecular orbital theory. Wiley, New York
25. Hay PJ, Wadt WR (1985) J Chem Phys 82:270-283
26. Perdew JP (1986) Phys Rev B 33:8822-8824
27. Alagona G, Ghio C, work in progress
28. Schultz NE, Zhao Y, Truhlar DG (2005) J Phys Chem A 109:11127-11143
29. London F (1937) J Phys Radium 8:397-409
30. McWeeny R (1962) Phys Rev 126:1028-1034
31. Ditchfield R (1974) Mol Phys 27:789-807
32. Dodds JL, McWeeny R, Sadlej AJ (1980) Mol Phys 41:1419-1430
33. Wolinski K, Hilton JF, Pulay P (1990) J Am Chem Soc 112:8251-8260
34. Rocchiccioli S (2006) Substrate induced Diastereoselectivity in Rhodium Catalyzed Hydroformylation, PhD Thesis, University of Pisa
35. Settambolo R, Caiazzo A, Lazzaroni R (2001) Tetrahedron Lett 42:4045-4048
36. Settambolo R, Miniati S, Lazzaroni R (2003) Synth Commun 33:2953-2961
37. Settambolo R, Guazzelli G, Mandoli A, Lazzaroni R (2004) Tetrahedron: Asymmetry 15:1821-1823
38. Tan KL, Bergman RG, Ellman JA (2002) J Am Chem Soc 124:3202-3203
39. Tan KL, Bergman RG, Ellman JA (2002) J Am Chem Soc 124:13964-13965
40. Wiedemann SH, Lewis JC, Ellman JA, Bergman RG (2006) J Am Chem Soc 128:2452-2462 (references therein)
41. Rybtchinski B, Oevers S, Montag M, Vigalok A, Rozenberg H, Martin JML, Milstein D (2001) J Am Chem Soc 123:9064-9077
42. Rybtchinski B, Cohen R, Ben-David Y, Martin JML, Milstein D (2003) J Am Chem Soc 125:11041-11050 (references therein)