Asymmetric synthesis of β-lactams by [2+2] cycloaddition using 1,4:3,6-dianhydro-d-glucitol (isosorbide) derived chiral pools

Tetrahedron

Volumn 63, Issue 16, 2007, Pages 3380-3388

  Shaikh, A L ^a   Kale, A S ^a   Shaikh, Md Abrar ^a   Puranik, Vedavati G ^a   Deshmukh, A R A S ^b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b Emcure Pharmaceuticals Limited   (India)

Author keywords

Asymmetric synthesis; Azetidinones; Imines; Ketenes; Staudinger reaction

Indexed keywords

(6 ACETOXYHEXAHYDROFURO[3,2 B]FURAN 3 YLOXY)ACETIC ACID; 1 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL)ETHANE 1,2 DIOLETHANE 1,2 DIOL; 1 (4 CHLOROPHENYL) 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 3 METHOXYAZETIDIN 2 ONE; 1 (4 CHLOROPHENYL) 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 3 PHENOXYAZETIDIN 2 ONE; 1 BENZYL 2 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 4 OXOAZETIDIN 3 YLACETATE; 1 BENZYL 3 BENZYLOXY 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL)AZETIDIN 2 ONE; 1 BENZYL 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 3 METHOXYAZETIDIN 2 ONE; 1 BENZYL 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 3 PHENOXYAZETIDIN 2 ONE; 2 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 1 (4 METHOXYPHENYL) 4 OXOAZETIDIN 3 YLACETATE; 2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOLE 4 CARBALDEHYDE; 3 ALLYLOXY 6 METHOXYHEXAHYDROFURO[3,2 B]FURAN; 3 BENZYLOXY 1 (4 CHLOROPHENYL) 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL)AZETIDIN 2 ONE; 3 BENZYLOXY 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 1 ( 4 METHOXYPHENYL)AZETIDIN 2 ONE; 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 1 (4 METHOXYPHENYL) 3 PHENOXYAZETIDIN 2 ONE; 4 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 3 METHOXY 1 (4 METHOXYPHENYL)AZETIDIN 2 ONE; 4 CHLORO N [(2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL)METHYLENE]BENZENAMINE; 6 (2 OXO 1,4 DIPHENYLAZETIDIN 3 YLOXY)HEXAHYDROFURO[3,2 B]FURAN 3 YLACETATE; 6 [1 (4 CHLOROPHENYL) 2 OXO 4 PHENYLAZETIDIN 3 YLOXY]HEXAHYDROFURO[3,2 B] FURAN 3 YLACETATE; 6 METHOXYHEXAHYDROFURO[3,2 B]FURAN 3 YLOXYACETIC ACID; ALDEHYDE; AZETIDINE DERIVATIVE; BETA LACTAM; ISOSORBIDE; KETENE DERIVATIVE; N [(2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL)METHYLENE] 4 METHOXYBENZENAMINE; N [(2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL)METHYLENE]PHENYLMETHANAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; DRUG MECHANISM; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 33947218419     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.022     Document Type: Article

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69. 22 Least squares refinement of scale, positional and anisotropic thermal parameters for non-hydrogen atom converged to R=0.0898, Rw=0.1746 for 3039 unique observed reflections. Hydrogen atoms were geometrically fixed. The refinements were carried out using SHELXL-97. X-ray analysis revealed the stereochemistry of the compound to be 3R, 4S at C3 and C4, respectively. The crystal structure for 16a has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 620045.