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Enantioselective approach to 3-substituted prolines

✍ Scribed by Theodore M Kamenecka; You-Jung Park; Linus S Lin; Thomas Lanza Jr.; William K Hagmann


Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
53 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis


Enantioselective synthesis of 3-substituted prolines was achieved starting from commercially available 3-hydroxy-(S)-2proline. Palladium-mediated couplings were used to introduce a variety of groups at C3 using the corresponding enol triflate derived from N-trityl 3-oxo-(S)-2-proline methyl ester. Cleavage of the trityl residue and hydrogenation provided final products with good to modest diastereoselectivity.


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