- Award ID(s):
- 1658517
- PAR ID:
- 10337042
- Date Published:
- Journal Name:
- Evolution
- Volume:
- 68
- Issue:
- 11
- ISSN:
- 0014-3820
- Page Range / eLocation ID:
- 3166 to 3183
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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Abstract A new diastereoselective route to 2‐aminotetrahydrofurans has been developed from
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Abstract A new diastereoselective route to 2‐aminotetrahydrofurans has been developed from
N ,O ‐dialkenylhydroxylamines. These intermediates undergo a spontaneous C−C bond‐forming [3,3]‐sigmatropic rearrangement followed by a C−O bond‐forming cyclization. A copper‐catalyzedN ‐alkenylation of anN ‐Boc‐hydroxylamine with alkenyl iodides, and a base‐promoted addition of the resultingN ‐hydroxyenamines to an electron‐deficient allene, provide modular access to these novel rearrangement precursors. The scope of this de novo synthesis of simple nucleoside analogues has been explored to reveal trends in diastereoselectivity and reactivity. In addition, a base‐promoted ring‐opening and Mannich reaction has been discovered to covert 2‐aminotetrahydrofurans to cyclopentyl β‐aminoacid derivatives or cyclopentenones.