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Literature DB >> 18974820

Sulfinimine-derived 2,3-diamino esters in the asymmetric synthesis of piperidine (2S,3S)-(+)-CP-99,994.

Franklin A Davis¹, Yanfeng Zhang, Danyang Li.

Abstract

Sulfinimine-derived, differentially protected, 2,3-diamino esters are useful building blocks for the asymmetric synthesis of heterocycles and is illustrated by an efficient synthesis of amino piperidine (+)-CP-99,994.

Entities: Chemical

Year: 2007 PMID： 18974820 PMCID： PMC2083654 DOI： 10.1016/j.tetlet.2007.08.132

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

17 in total

Review 1. Substance P: structure, function, and therapeutics.

Authors: Prasanna Datar; Sudha Srivastava; Evans Coutinho; Girjesh Govil
Journal: Curr Top Med Chem Date: 2004 Impact factor: 3.295

2. Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.

Authors: Akihiro Okada; Tomoyuki Shibuguchi; Takashi Ohshima; Hyuma Masu; Kentaro Yamaguchi; Masakatsu Shibasaki
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

Review 3. Alpha,beta-diamino acids: biological significance and synthetic approaches.

Authors: Alma Viso; Roberto Fernández de la Pradilla; Ana García; Aida Flores
Journal: Chem Rev Date: 2005-08 Impact factor: 60.622

4. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

Authors: Ahmed F. Abdel-Magid; Kenneth G. Carson; Bruce D. Harris; Cynthia A. Maryanoff; Rekha D. Shah
Journal: J Org Chem Date: 1996-05-31 Impact factor: 4.354

5. Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.

Authors: Franklin A Davis; He Xu; Junyi Zhang
Journal: J Org Chem Date: 2007-02-17 Impact factor: 4.354

Review 6. Adventures in sulfur-nitrogen chemistry.

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

7. 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

8. Nucleophilic addition to 3-substituted pyridinium salts: expedient syntheses of (-)-L-733,061 and (-)-CP-99,994.

Authors: Alexandre Lemire; Michel Grenon; Mehrnaz Pourashraf; André B Charette
Journal: Org Lett Date: 2004-09-30 Impact factor: 6.005

9. Asymmetric synthesis of syn-(2R,3S)-and anti-(2S,3S)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates.

Authors: Franklin A Davis; Jianghe Deng
Journal: Org Lett Date: 2004-08-05 Impact factor: 6.005

Sulfinimine-derived 2,3-diamino esters in the asymmetric synthesis of piperidine (2S,3S)-(+)-CP-99,994.

Review 1. Substance P: structure, function, and therapeutics.

2. Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.

Review 3. Alpha,beta-diamino acids: biological significance and synthetic approaches.

4. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

5. Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.

Review 6. Adventures in sulfur-nitrogen chemistry.

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

8. Nucleophilic addition to 3-substituted pyridinium salts: expedient syntheses of (-)-L-733,061 and (-)-CP-99,994.

9. Asymmetric synthesis of syn-(2R,3S)-and anti-(2S,3S)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates.

10. Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon.

1. A Highly Divergent Synthesis of 3-Aminotetrahydropyridines.

2. Synthesis of (+)-CP-99,994 via Pd(0)-catalyzed asymmetric allylic and homoallylic C-H Diamination of terminal olefin.

3. alpha-Amino 1,3-Dithioketal Mediated Asymmetric Synthesis of Piperidines (L-733,060) and Tetrahydrofuran Glycines.

4. Asymmetric synthesis of (2S,3R)-(-)-epi-CP-99,994 using sulfinimine-derived anti-2,3-diamino esters.

Review 5. Applications of aryl-sulfinamides in the synthesis of N-heterocycles.