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Volumn 10, Issue 14, 2008, Pages 3021-3023

A direct and versatile access to α,α-disubstituted 2-pyrrolidinylmethanols by SmI2-mediated reductive coupling

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EID: 59949098435     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800982n     Document Type: Article
Times cited : (40)

References (40)
  • 16
    • 0000311992 scopus 로고    scopus 로고
    • For other examples of synthesis of α,α-disubstituted 2-pyrrolidinylmethanols from reaction of 2-lithiopyrrolidines with symmetrical ketones or aldehydes, see also: (a) Reitz, D. B.; Beak, P.; Tse, A. J. Org. Chem. 1981, 46, 4316.
    • For other examples of synthesis of α,α-disubstituted 2-pyrrolidinylmethanols from reaction of 2-lithiopyrrolidines with symmetrical ketones or aldehydes, see also: (a) Reitz, D. B.; Beak, P.; Tse, A. J. Org. Chem. 1981, 46, 4316.
  • 22
  • 32
    • 59949091325 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of α,α-Disubstituted 2-Pyrrolidinylmethanols 2-7. Method A (for aromatic ketones, To a stirred and carefully deoxygenated solution of the nitrone 1 (60 mg, 0.7 mmol) and aromatic ketone (0.5 mmol) in dry THF was added a 0.1 M solution of SmI2 (11.0 mL, 1.1 mmol) at -78°C under argon. After 15 min, degassed water (36 μL, 2.0 mmol) and SmI2 (14.0 mL, 1.4 mmol) were added, and the reaction mixture was allowed to reach room temperature. After 1 h, a saturated solution of Na2S2O3 (5 mL) and 1 M NaOH solution (15 mL) were added, and the mixture was extracted with EtOAc (20 mL, Usual workup yielded racemic products 2-5. Method B (for aliphatic ketones, Same procedure as for method A, but degassed water (90 μL, 5.0 mmol) was added at the beginning of the reaction products 6 and 7
    • 3 (5 mL) and 1 M NaOH solution (15 mL) were added, and the mixture was extracted with EtOAc (20 mL). Usual workup yielded racemic products 2-5. Method B (for aliphatic ketones): Same procedure as for method A, but degassed water (90 μL, 5.0 mmol) was added at the beginning of the reaction (products 6 and 7).
  • 35
    • 59949095587 scopus 로고    scopus 로고
    • 2 reaction mixture; see the Supporting Information.
    • 2 reaction mixture; see the Supporting Information.
  • 39
    • 59949097022 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 40
    • 59949083856 scopus 로고    scopus 로고
    • Determined by chiral HPLC on a Daicel Chiralpak AD-RH column, acetonitrile/water; see the Supporting Information
    • Determined by chiral HPLC on a Daicel Chiralpak AD-RH column, acetonitrile/water; see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.