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1,3-Dipolar Cycloadditions of a 2-Oxoethanenitrile Oxide Derived from (2R)-Bornane-10,2-sultam to Electronically Modified 4,4′-Disubstituted Stilbenes

✍ Scribed by Jan Romanski; Christian Chapuis; Janusz Jurczak

Publisher: John Wiley and Sons
Year: 2009
Tongue: German
Weight: 362 KB
Volume: 92
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200800412

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✦ Synopsis

Thanks to its type-II dipole nature, we were able to demonstrate the higher reactivity of the SO 2 / C¼O syn-conformer for the uncatalyzed 1,3-dipolar cycloaddition of the 2-oxoethanenitrile oxide 2 derived from bornane-10,2-sultam to the symmetric 4,4'-disubstituted trans-stilbenes 3a -3i. The C(a)-si dipolarophile p y approach along the C¼O bond precludes the use of the steric rules formerly expressed for this pseudo-C 2 -symmetric auxiliary. The observed diastereoselectivity is related to the electronic nature of the dipolarophile and may be predicted on the basis of its s para Hammett constant. The absolute configuration was based on the X-ray structure analysis of cycloadduct (4S,5S)-4b, which exhibits an SO 2 / C¼O anti-conformation. Finally, the results obtained with cis-stilbene suggest a nonsynchronous mechanism.

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