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Literature DB >> 16496997

5-Carboxy-2-azabicyclo[2.1.1]hexanes as precursors of 5-halo, amino, phenyl, and 2-methoxycarbonylethyl methanopyrrolidines.

Grant R Krow¹, Qiuli Huang, Guoliang Lin, Ryan A Centafont, Andrew M Thomas, Deepa Gandla, Charles Debrosse, Patrick J Carroll.

Abstract

Novel 5-X-substituted-2-azabicyclo[2.1.1]hexanes (X = 5-syn-Cl, -Br, -I, -Ph, -NHCOOR (R = Me, Bn, t-Bu), -CH2CH2COOMe and X = 5-anti-Br, -I, -Ph) were synthesized from the X = 5-syn-carboxy derivative. New 5-anti-X-2-azabicyclo[2.1.1]hexanes, X = NHCOOR (R = Me, Bn), were prepared stereoselectively from the X = 5-anti-carboxy substrate.

Entities: Chemical

Mesh：

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Year: 2006 PMID： 16496997 DOI： 10.1021/jo052506b

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

5 in total

1. Synthesis of 5-fluoro- and 5-hydroxymethanoprolines via lithiation of N-BOC-methanopyrrolidines. Constrained Cγ-exo and Cγ-endo Flp and Hyp conformer mimics.

Authors: Grant R Krow; Matthew D Shoulders; Ramakrishna Edupuganti; Deepa Gandla; Fang Yu; Philip E Sonnet; Matthew Sender; Amit Choudhary; Charles DeBrosse; Charles W Ross; Patrick Carroll; Ronald T Raines
Journal: J Org Chem Date: 2012-05-25 Impact factor: 4.354

2. Synthesis of conformationally constrained 5-fluoro- and 5-hydroxymethanopyrrolidines. Ring-puckered mimics of gauche- and anti-3-fluoro- and 3-hydroxypyrrolidines.

Authors: Grant R Krow; Ram Edupuganti; Deepa Gandla; Fang Yu; Matthew Sender; Philip E Sonnet; Michael J Zdilla; Charles DeBrosse; Kevin C Cannon; Charles W Ross; Amit Choudhary; Matthew D Shoulders; Ronald T Raines
Journal: J Org Chem Date: 2011-04-18 Impact factor: 4.354

5-Carboxy-2-azabicyclo[2.1.1]hexanes as precursors of 5-halo, amino, phenyl, and 2-methoxycarbonylethyl methanopyrrolidines.

1. Synthesis of 5-fluoro- and 5-hydroxymethanoprolines via lithiation of N-BOC-methanopyrrolidines. Constrained Cγ-exo and Cγ-endo Flp and Hyp conformer mimics.

2. Synthesis of conformationally constrained 5-fluoro- and 5-hydroxymethanopyrrolidines. Ring-puckered mimics of gauche- and anti-3-fluoro- and 3-hydroxypyrrolidines.

3. Decarboxylative Halogenation of Organic Compounds.

4. Conformational preferences of substrates for human prolyl 4-hydroxylase.

5. 5(6)-anti-Substituted-2-azabicyclo[2.1.1]hexanes: a nucleophilic displacement route.