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New and Stereoselective Synthesis of 1,4-Disubstituted Buten-4-ols (Homoallylic Alcohol α-Adducts) from the Corresponding γ-Isomers (3,4-Disubstituted Buten-4-ols) via an Acid-Catalyzed Allyl-Transfer Reaction with Aldehydes

Shin-ichi Sumida, Masanori Ohga, Junji Mitani and Junzo Nokami

*Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Okayama 700-0005, Japan

S.-i. Sumida, M. Ohga, J. Mitani, J. Nokami, J. Am. Chem. Soc., 2000, 122, 1310-1313.

DOI: 10.1021/ja990057p

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γ-Adducts of homoallylic alcohols were converted to the corresponding α-adducts by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti- and syn-γ-adducts gave E- and Z-α-adducts, respectively, and the optical purity was transferred to the α-adducts This suggests that the allyl-transfer reaction proceeds stereoselectively via a six-membered cyclic transition state.

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Stereochemistry of the Allyl Transfer

Key Words

homoallylic alcohols

ID: J48-Y2000