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Facile, regio and stereoselective Diels-Alder reactions of allenic trichloromethyl sulfones and sulfoxides

✍ Scribed by Samuel Braverman; Zvi Lior

Book ID
104214696
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
305 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

lk a?enophiiic reactiviv of allenes is bastically increased by the powerful eleclron wifh&awing dichloromelhylsu@qv~ or suljbyl suklituents.

Ihe f44+2/-crcroaririitions proceed snoofhly with high regio-and stereoselectivity under miki conditions. Using an opiicdy active allenyl surfosle. tran$er of chiraiity bar been observed

Because of its remarkable synthetic utility, the Diels-Alder reaction continues to attract wide attention.2 The use of allenes as dienophiles provides an attractive approach to the synthesis of various methylenecyclohexanes which are useful building blocks of terpenoid natural products.3 However, the use of allenes in the past was limited by the need of drastic conditions, due to their low dienophilic reactivity.

Recent MNDO calculations for methanesulfonylp~padiene indicate that the introduction of a sulfbnyl group causes a remarkable lowering of the LUMO energy level campared with allene (AE = 3.07 ev), with

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