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Chelate-Controlled Mukaiyama Reactions with Chiral β-Formyl Esters

DOI: 10.1016/0040-4020(92)80019-C

Source and publish data:

Tetrahedron p. 5681 - 5690 (1992)

Update date:2022-08-16

Topics:

Authors:

Angert, HubertAngert, Hubert

Kunz, ThomasKunz, Thomas

Reissig, Hans-UlrichReissig, Hans-Ulrich

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Article abstract of DOI:10.1016/0040-4020(92)80019-C

Additions of silyl enol ethers 3, 6, and 8 to chiral β-formyl esters 1 in the presence of TiCl4 provide trans-γ-lactones 4, 7, and 9 in high yield and with good to excellent diastereofacial selectivity.This high trans-preferrence is due to effective chelate-control involving seven-membered ring 1-TiCl4 complexes.

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Full text of DOI:10.1016/0040-4020(92)80019-C

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