Synthesis of Optically Active 2‐Siloxycyclopropanecarboxylates by Asymmetric Catalysis, IV. – Influence of Nucleophilicity of Silyl Enol Ethers on Stereoselectivities in Asymmetric Cyclopropanation Reactions | Zendy

Schumacher Ralf | Zendy; Reißig HansUlrich | Zendy

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Synthesis of Optically Active 2‐Siloxycyclopropanecarboxylates by Asymmetric Catalysis, IV. – Influence of Nucleophilicity of Silyl Enol Ethers on Stereoselectivities in Asymmetric Cyclopropanation Reactions

Author(s) -

Schumacher Ralf,

Reißig HansUlrich

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970312

Subject(s) - cyclopropanation , chemistry , nucleophile , enol , silylation , nitro , medicinal chemistry , cationic polymerization , electrophile , catalysis , aryl , trifluoromethyl , organic chemistry , stereochemistry , alkyl

By variation of the aryl substituents of silyl enol ethers 1a–e and 1f–k , the influence of their nucleophilicity on the stereochemical outcome of cyclopropanation reactions was studied. Using the neutral Schiff‐base catalyst 2 · Cu(OAc) 2 , there was only a weak effect. On the other hand, with the cationic bisoxazoline complex 3 · CuOTf a remarkable increase in the enantioselectivity was observed with more strongly electron‐attracting substituents such as a trifluoromethyl or nitro group.

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