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Volumn 63, Issue 21, 1998, Pages 7128-7129

Highly diastereoselective epoxidation of ketene dithioacetal dioxides: A new approach to the asymmetric synthesis of α-amino amides

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EID: 0000137347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9814896     Document Type: Article
Times cited : (37)

References (36)
  • 1
    • 0028355337 scopus 로고
    • For a review on the synthesis of α-amino acids, see: Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
    • (1994) Tetrahedron , vol.50 , pp. 1539-1650
    • Duthaler, R.O.1
  • 15
    • 85034475814 scopus 로고
    • Cyclization to give an epoxide does occur if only one sulfinyl group is present; for a review, see: Satoh, T.; Yamakawa, K Synlett 1992, 455-468.
    • (1992) Synlett , pp. 455-468
    • Satoh, T.1    Yamakawa, K.2
  • 21
    • 33744841353 scopus 로고    scopus 로고
    • note
    • Oxidation of 2-carboethoxy-1,3-dithiane and other 2-substituted 1,3-dithanes with (+)-DET gave the (R)-sulfoxide as noted in refs 17, 18, and 32.
  • 25
    • 33744849778 scopus 로고    scopus 로고
    • Cesium carbonate, DBU, Methylamine, anhydrous potassium carbonate, n-butyllithium, tert-butylmagnesium chloride, lithium hydroxide, magnesium hydroxide, lithium ethoxide, and magnesium hydroxide were all tried
    • Cesium carbonate, DBU, Methylamine, anhydrous potassium carbonate, n-butyllithium, tert-butylmagnesium chloride, lithium hydroxide, magnesium hydroxide, lithium ethoxide, and magnesium hydroxide were all tried.
  • 26
    • 33744848829 scopus 로고    scopus 로고
    • Anhydrous LiOH and the monohydrate proved equally effective. This base has been used previously in the Wadsworth-Emmons reaction of esterstabilized phosphonate carbanions.33 Magnesium hydroxide proved to be an equally effective base, but only when used in the presence of water (e.g., 5% water in THF). Under the same conditions (5% water in THF), LiOH was much less effective
    • Anhydrous LiOH and the monohydrate proved equally effective. This base has been used previously in the Wadsworth-Emmons reaction of esterstabilized phosphonate carbanions.33 Magnesium hydroxide proved to be an equally effective base, but only when used in the presence of water (e.g., 5% water in THF). Under the same conditions (5% water in THF), LiOH was much less effective.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.