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Stereoselective syntheses of heterocycles with lithiated methoxyallene

✍ Scribed by Hans-Ulrich Reissig; Stephan Hormuth; Wolfgang Schade; Marlyse Okala Amombo; Toshiko Watanabe; Robert Pulz; Arndt Hausherr; Reinhold Zimmer

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
452 KB
Volume
37
Category
Article
ISSN
0022-152X

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## Abstract Addition of lithiated methoxyallene 2 to optically active __N__‐benzyl‐Boc‐protected amino aldehydes 12–14 and to aldehyde 16 provides products 17–20 with good to excellent diastereoselectivity. These adducts are subsequently cleaved by ozonolysis to give α‐hydroxy‐β‐amino acid derivati

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Lithiated furans have been found to cleave the S-S bond of polymerization-resistant 1,2dithiolanes to give the ring opened products in good yields. In the case of lithiated benzofuran, the excess reagent reacted with the normal product to give a mixture. Lithiated dihydrofuran and dihydropyran gave