Several allyl heteroarylalkyl ethers have been synthesized and then deprotonated with nBuLi in THF at -78°C to give lithium derivatives. The lithium-bearing terminus was either the α- or the α′-carbon atom, depending on the associated proton acidity. In the absence of an external electrophile, a sigmatropic rearrangement occurs, generating a new C-C bond. Heteroarylalkyl homoallylic alcohols and allyl heteroarylalkylic alcohols were obtained as products of stereoselective [2,3]- or [1,2]-Wittig rearrangements, respectively. Homoallylic alcohols were obtained in high yields and with fairly good enantiomeric enrichments when the reactions were carried out in toluene with (-)-sparteine as the external chiral ligand

A Highly Stereoselective Synthesis of alpha-beta-Unsaturated Oxazolines

CAPRIATI, Vito;DEGENNARO, LEONARDO;LUISI, Renzo
2001-01-01

Abstract

Several allyl heteroarylalkyl ethers have been synthesized and then deprotonated with nBuLi in THF at -78°C to give lithium derivatives. The lithium-bearing terminus was either the α- or the α′-carbon atom, depending on the associated proton acidity. In the absence of an external electrophile, a sigmatropic rearrangement occurs, generating a new C-C bond. Heteroarylalkyl homoallylic alcohols and allyl heteroarylalkylic alcohols were obtained as products of stereoselective [2,3]- or [1,2]-Wittig rearrangements, respectively. Homoallylic alcohols were obtained in high yields and with fairly good enantiomeric enrichments when the reactions were carried out in toluene with (-)-sparteine as the external chiral ligand
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/131702
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