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Proline catalyzed sequential α-amination/ Prins/ Ritter amidation of aldehydes : new method of construction of tetrahydropyran units

By: Ahuja, Brijbhushan.
Contributor(s): Gadakh, Sunita.
Publisher: New Delhi CSIR 2019Edition: Vol.58B(9), Sep.Description: 1019-1028p.Subject(s): GENERAL CHEMISTRYOnline resources: Click here In: Indian journal of chemistry (Section B)Summary: An efficient “one-pot” synthetic method toward highly substituted tetrahydrofuran (THP) units is reported. The key transformation involves an atom-efficient sequential proline catalyzed α-amination of aldehydes to give α-aminated aldehydes in situ and the subsequent cyclomerization with homoallylic alcohols under Prins/Ritter conditions. Notably, this method provides access to enantiopure 1,2-syn and 1,4-anti diamino alcohols via reductive ring opening of THP units.
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An efficient “one-pot” synthetic method toward highly substituted tetrahydrofuran (THP) units is reported. The key transformation involves an atom-efficient sequential proline catalyzed α-amination of aldehydes to give α-aminated aldehydes in situ and the subsequent cyclomerization with homoallylic alcohols under Prins/Ritter conditions. Notably, this method provides access to enantiopure 1,2-syn and 1,4-anti diamino alcohols via reductive ring opening of THP units.

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