Stereoselective Diels–Alder reactions of 3-phosphonopropenoyl derivatives of 1,3-oxazolidin-2-ones

Dienophiles of the general structure (EtO) 2P(O)CH CHCOX have been prepared, where X represents an oxazolidinone chiral auxiliary. Use of the ( S)-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one auxiliary gave Diels–Alder adducts with several cyclic and acyclic dienes. The crystal structures of the ma...

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Bibliographic Details
Published in:Tetrahedron 2006-12, Vol.62 (52), p.12398-12407
Main Authors: Cheng, Eileen W.C., Mandalia, Reena T., Motevalli, Majid, Mothia, Begum, Patanwadia, Yashvant, Wyatt, Peter B.
Format: Article
Language:English
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Summary:Dienophiles of the general structure (EtO) 2P(O)CH CHCOX have been prepared, where X represents an oxazolidinone chiral auxiliary. Use of the ( S)-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one auxiliary gave Diels–Alder adducts with several cyclic and acyclic dienes. The crystal structures of the main cyclohexa-1,3-diene and 2,3-dimethylbutadiene adducts formed during reactions in the presence of dialkylaluminium halides are consistent with a reaction, which is stereoselectively endo with respect to the carbonyl group and occurs on the less hindered face of the dienophile when aluminium is chelated between the two carbonyl groups. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.09.099