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Diels-alder reaction of chiral dienes. Remarkable effect of dienophile polarity upon diastereo face selectivity

✍ Scribed by Tatsuo Hamada; Hiroki Sato; Masataka Hikota; Osamu Yonemitsu

Book ID
104244989
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
184 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Face selectivity of Diels-Alder reaction of diene having the stereogenic center at allylic position depends on dienophile polarity, and hetero Diels-Alder reaction with dienophile such as N-tosylimine and Ntosylsulfinylimine was found to give exclusively ul product. The reaction mechanism and empirical rule of the face selectivity of these reactions are discussed.

Recently, diastereoselective reactions to chiral allylic alcohols or ethers are under active investigation to develop new methodologies for the total syntheses of complex natural products containing many chiral centers 1.

However, there has been little study so far of diene syntheses of chiral diene in spite of their synthetic

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