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Volumn , Issue 5, 2009, Pages 0767-0770

Chirality transfer in azetidinium ylides: An enantioselective route to α-quaternary azetidines

Author keywords

Azetidines; Nitrogen ylides; quaternary amino acids

Indexed keywords

EID: 62349094712 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087939 Document Type: Article

Times cited : (21)

References (28)

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- Compounds 17 and 20 were obtained as a 6:4 ratio of epimers by anionic cyclization of the corresponding chloride, obtained following a similar synthetic sequence as the one described in Scheme 1. Compound 22 was obtained as the major epimer (7:3 ratio) following Scheme 1.
- Compounds 17 and 20 were obtained as a 6:4 ratio of epimers by anionic cyclization of the corresponding chloride, obtained following a similar synthetic sequence as the one described in Scheme 1. Compound 22 was obtained as the major epimer (7:3 ratio) following Scheme 1.

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- The crystal structure data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 703601
- The crystal structure data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 703601.

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28
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- General Procedure for Rearrangement of Azetidinium Triflates The following procedure for the preparation of azetidine 13 is representative. To a solution of azetidinium triflate 10 (823 mg, 2.19 mmol) in dry THF (40 mL, cooled at -78°C was added in one portion KOt-Bu (300 mg, 2.67 mmol, The reaction mixture was allowed to reach 0°C over 3 h and was quenched by addition of H2O and Et 2O. The reaction mixture was extracted with Et2O, the combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude residue was examined by 1H NMR and showed a diastereomeric ratio of 98:2. Purification by flash chromatography (cyclohexane-EtOAc, 8:2) gave 13 as a colorless oil (461mg, 93, Selected Data Compound 13: Rf, 0.48 (cyclohexane-EtOAc, 8:2, α]D25 -13.1 c 0.33, CHCl3
- + - HCN].

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