4.5 Article

Stereoselective Conjugate Addition-Enamination of α-Linear N-tert-Butanesulfinyl Ketimines with Nitroolefins

期刊

SYNTHESIS-STUTTGART
卷 54, 期 19, 页码 4361-4370

出版社

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1719925

关键词

N-sulfinyl metalloenamines; conjugate addition; deprotonation; enamination; stereoselectivity

资金

  1. National Natural Science Foundation of China [22161048, 21871292]
  2. Yunnan University

向作者/读者索取更多资源

N-Sulfinyl metalloenamines, generated by deprotonating alpha-linear N-tert-butariesulfinyl ketimines, reacted with nitroalkenes via stereoselective conjugate addition to give Michael adducts with opposite stereochemistry. In the presence of excess base, the adducts derived from alpha-linear ketimines were further stereoselectively deprotonated to afford N-sulfinyl (Z)-enamine derivatives with good yields and stereoselectivities. A reaction model was proposed to rationalize the observed stereochemistry.
N-Sulfinyl metalloenamines, generated by deprotonating alpha-linear N-tert-butariesulfinyl ketimines, reacted with nitroalkenes via stereoselective conjugate addition to give Michael adducts with opposite stereochemistry to that obtained using alpha-branched sulfinylketimines. in the presence of excess base (2.5 equiv t-BuOK), the adducts derived from alpha-linear ketimines were further stereoselectively deprotonated to afford the corresponding kinetically favorable N-sulfinyl (Z)-enamine derivatives in good yields with good stereoselectivities. A reaction model was proposed to rationalize the observed stereochemistry.

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