Lewis acid-promoted intermolecular carbonyl-ene reaction of enantiopure 4-oxoazetidine-2-carbaldehydes. Rapid entry to novel fused polycyclic β-lactams

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3106-3111

  Alcaide, Benito ^a   Almendros, Pedro ^b   Pardo, Carmen ^a   Rodríguez Ranera, Carolina ^a   Rodríguez Vicente, Alberto ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL REACTIONS; OLEFINS; STEREOCHEMISTRY;

DIELS-ALDER REACTIONS;

ALDEHYDES;

4 [(1' HYDROXY)HOMOLALLYL] BETA LACTAM DERIVATIVE; 4 OXOAZETIDINE 2 CARBALDEHYDE DERIVATIVE; ALDEHYDE DERIVATIVE; BETA LACTAM DERIVATIVE; CARBONYL DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOMER; STEREOCHEMISTRY;

EID: 0344519741     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0340509     Document Type: Article

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56. Synthesis of medium-sized rings, notably eight- and nine-membered ring systems, has usually been hampered by entropic/enthalpic factors and transannular interactions between the methylene groups. For reviews, see: (a) Galli, L.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. (b) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95. In view of these difficulties, the synthesis of these structures still remains a partially unsolved problem. For selected reviews on medium-sized ring preparation, see: (c) Yet, L. Chem. Rev. 2000, 100, 2963. (d) Molander, G. Acc. Chem. Res. 1998, 31, 603. (e) Lautens, M. Top. Curr. Chem. 1997, 190, 1.
57. Synthesis of medium-sized rings, notably eight- and nine-membered ring systems, has usually been hampered by entropic/enthalpic factors and transannular interactions between the methylene groups. For reviews, see: (a) Galli, L.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. (b) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95. In view of these difficulties, the synthesis of these structures still remains a partially unsolved problem. For selected reviews on medium-sized ring preparation, see: (c) Yet, L. Chem. Rev. 2000, 100, 2963. (d) Molander, G. Acc. Chem. Res. 1998, 31, 603. (e) Lautens, M. Top. Curr. Chem. 1997, 190, 1.
58. Synthesis of medium-sized rings, notably eight- and nine-membered ring systems, has usually been hampered by entropic/enthalpic factors and transannular interactions between the methylene groups. For reviews, see: (a) Galli, L.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. (b) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.In view of these difficulties, the synthesis of these structures still remains a partially unsolved problem. For selected reviews on medium-sized ring preparation, see: (c) Yet, L. Chem. Rev. 2000, 100, 2963. (d) Molander, G. Acc. Chem. Res. 1998, 31, 603. (e) Lautens, M. Top. Curr. Chem. 1997, 190, 1.
59. Synthesis of medium-sized rings, notably eight- and nine-membered ring systems, has usually been hampered by entropic/enthalpic factors and transannular interactions between the methylene groups. For reviews, see: (a) Galli, L.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117. (b) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.In view of these difficulties, the synthesis of these structures still remains a partially unsolved problem. For selected reviews on medium-sized ring preparation, see: (c) Yet, L. Chem. Rev. 2000, 100, 2963. (d) Molander, G. Acc. Chem. Res. 1998, 31, 603. (e) Lautens, M. Top. Curr. Chem. 1997, 190, 1.
60. Only examples available have been recently reported by us. See ref 15.
61. Compounds 6, 7, 11, and 12 showed values of coupling constants and NOE enhancements in good agreement with those reported for analogous systems. See refs 14 and 15.
62. Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in Supporting Information.