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Diastereoselective [4 + 2]Cycloaddition of Cyclopentadiene to N-Tosyliminoacetyl Derivatives of Chiral Secondary Alcohols.

✍ Scribed by S. Szymanski; M. Marzec; J. Jurczak

Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
33
Category
Article
ISSN
0931-7597

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✦ Synopsis

Abstract

For Abstract see ChemInform Abstract in Full Text.

πŸ“œ SIMILAR VOLUMES

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Asymmetric induction in the [4+2]cycloaddition of cyclopentadiene and furan to chiral derivatives of fumaric acid
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## Abstract [4+2]Cycloaddition reactions of cyclopentadiene (**1a**) and furan (**1b**) to __N,Nβ€²__‐fumaroyldi[(2__R__)‐bornane‐10,2‐sultam] (**2**) and to __N,Nβ€²__‐fumaroyldi[(2__R__)‐bornane‐10,2‐(2′‐phenyl‐pyrazol‐3′‐one)] (**3**) are presented. A correlation between the solvent polarity and the

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The [4 2] cycloaddition of cyclopentadiene to the (2R )-bornane-10,2-sultam derivative (Γ€)-1b of fumaric monomethyl ester proceeds with high endo and p-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl 4 . The major diastereoisomer endo-(2R,3R )-2b, isolated in 87% yield by cryst