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2,5-Diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions

✍ Scribed by Thuy X.H. Le; Jacqueline C. Bussolari; William V. Murray

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
177 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Diketopiperazines have been utilized as chiral auxiliaries for asymetric Diels-Alder reactions. Cyclo-Sphenylalanyl-R-proline (2) was found to be the most promising of these auxiliaries and afforded Diels-Alder adducts in high chemical yield (78 -95%), with endo selectivities generally greater than 9:1. The diastereoselectivities observed were comparable to the best previously published values.

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