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• W2949071330 startingPage "8037" @default.
• W2949071330 abstract "An asymmetric synthesis of fused bicyclic amino acids having a hexahydro-cyclopenta[c]pyridine skeleton and carrying besides an enone structural element a substituent at the beta-position is described. The key steps of the synthesis are a highly selective allylation of N-tert-butylsulfonyl imino ester with bis(allylsulfoximine)titanium complexes and a highly diastereoselective Pauson-Khand cycloaddition of sulfonimidoyl-substituted gamma,delta-unsaturated alpha-amino acid esters carrying a substituent at the beta-position and a propargyl group at the N-atom. The cyclization is accompanied by a reductive cleavage of the sulfoximine group of the primary cyclization product. Surprisingly, the removal of the sulfoximine group proceeds with inversion of the configuration at the S-atom and gives N-methyl-phenylsulfinamide with >/=98% ee. Deprotection of the bicyclic N-tert-butylsulfonyl-protected amino acid ester was accomplished through treatment with CF(3)SO(3)H under anhydrous conditions. The enantio- and diastereomerically pure sulfoximine-substituted gamma,delta-unsaturated alpha-amino acid esters used as starting material were obtained through a highly regio- and diastereoselective allylation of N-tert-butylsulfonyl imino ester with acyclic bis(allylsulfoximine)titanium complexes, described previously." @default.
• W2949071330 created "2019-06-27" @default.
• W2949071330 creator A5030680351 @default.
• W2949071330 creator A5052953262 @default.
• W2949071330 date "2003-09-26" @default.
• W2949071330 modified "2023-10-15" @default.
• W2949071330 title "Asymmetric Synthesis of Fused Bicyclic α-Amino Acids Having a Hexahydro-cyclopenta[<i>c</i>]pyridine Skeleton via Intramolecular Pauson−Khand Reaction of 1-Sulfonimidoyl-Substituted 5-Azaoct-1-en-7-ynes" @default.
• W2949071330 cites W1967214834 @default.
• W2949071330 cites W1970433380 @default.
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• W2949071330 cites W1978984877 @default.
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• W2949071330 doi "https://doi.org/10.1021/jo030171x" @default.
• W2949071330 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/14535780" @default.
• W2949071330 hasPublicationYear "2003" @default.
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