Regulation of cyclization for the stereoselective synthesis of substituted tetrahydrofurans and tetrahydrooxepines.
Dramatic solvent effect is observed during the cyclization of 1. Synthesis of 2 is achieved from the reaction of 1 with a hexamethylditin-catalyzed palladium complex followed by aldehydes in the presence of TMSOTf in THF, whereas 3 is formed in CH2Cl2. The method described herein is successful with various substrates 1 in good yields and high levels of diastereoselectivity.
Kim
Sang-Hoon
SH
BK-21 School of Chemical Materials Science and Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea.
Oh
Seung-Ju
SJ
Ho
Pil-Su
PS
Kang
Sin-Cheol
SC
O
Kyung-Jin
KJ
Yu
Chan-Mo
CM