Literature DB >> 19278245

Asymmetric synthesis of substituted tropinones using the intramolecular mannich cyclization reaction and acyclic N-sulfinyl beta-amino ketone ketals.

Franklin A Davis1, Naresh Theddu, Paul M Gaspari.   

Abstract

Sulfinimine-derived, enantiopure N-sulfinyl beta-amino ketone ketals on hydrolysis give dehydropyrrolidine ketones that on treatment with (Boc)(2)O/DMAP afford substituted tropinones in good yield.

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Year:  2009        PMID： 19278245      PMCID： PMC2753232          DOI： 10.1021/ol9002948

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

1.  Enantioselective synthesis of unnatural (S)-(+)-cocaine.

Authors:  J C Lee; K Lee; J K Cha
Journal:  J Org Chem       Date:  2000-07-28       Impact factor: 4.354

2.  delta-Amino beta-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis. Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A.

Authors:  F A Davis; B Chao; T Fang; J M Szewczyk
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

3.  Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides.

Authors:  Franklin A Davis; M Brad Nolt; Yongzhong Wu; Kavirayani R Prasad; Danyang Li; Bin Yang; Kerisha Bowen; Seung H Lee; John H Eardley
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

4.  Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis of proline and pipecolic acid derivatives.

Authors:  F A Davis; H Zhang; S H Lee
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

Review 5.  Adventures in sulfur-nitrogen chemistry.

Authors:  Franklin A Davis
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

6.  Asymmetric synthesis of alpha-substituted beta-amino ketones from sulfinimines (N-sulfinyl imines). synthesis of the indolizidine alkaloid (-)-223A.

Authors:  Franklin A Davis; Bin Yang
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

7.  Direct asymmetric synthesis of beta-amino ketones from sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B.

Authors:  Franklin A Davis; Bin Yang
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

8.  Synthetic approaches to the polycyclic alkaloid stemofoline.

Authors:  Alison M Baylis; Michael P H Davies; Eric J Thomas
Journal:  Org Biomol Chem       Date:  2007-08-14       Impact factor: 3.876

9.  Total synthesis of (+)-cocaine via desymmetrization of a meso-dialdehyde.

Authors:  Douglas M Mans; William H Pearson
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

10.  Asymmetric synthesis of cyclic alpha-amino phosphonates using masked oxo sulfinimines (N-sulfinyl imines).

Authors:  Franklin A Davis; Seung H Lee; He Xu
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354
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  2 in total

Review 1.  Applications of aryl-sulfinamides in the synthesis of N-heterocycles.

Authors:  Rose Mary Philip; G S Susan Treesa; Salim Saranya; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-06-08       Impact factor: 4.036

2.  Organocatalytic Enantioselective γ-Position-Selective Mannich Reactions of β-Ketocarbonyl Derivatives.

Authors:  Venkati Bethi; Fujie Tanaka
Journal:  Org Lett       Date:  2022-09-12       Impact factor: 6.072
  2 in total

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