Literature DB >> 33575984

Fukuyama reduction, Fukuyama coupling and Fukuyama-Mitsunobu alkylation: recent developments and synthetic applications.

Sana Sikandar1, Ameer Fawad Zahoor2, Shazia Naheed1, Bushra Parveen1, Kulsoom Ghulam Ali1, Rabia Akhtar1.   

Abstract

Fukuyama reaction for the synthesis of multifunctional aldehydes, secondary amines and ketones has gained considerable importance in synthetic organic chemistry because of mild reaction conditions. The use of thioesters in both Fukuyama aldehydes and ketones synthesis is highly attractive for organic chemists as they are easily accessible from corresponding carboxylic acids. Fukuyama-Mitsunobu reaction utilizes 2-nitrobenzenesulfonyl (Ns) for the protection/activation/deprotection of primary amines to afford secondary amines in good yields and high enantioselectivities. This review presents recent synthetic developments and applications of Fukuyama reaction for the synthesis of aldehydes, secondary amines and ketones.
© 2021. The Author(s), under exclusive licence to Springer Nature Switzerland AG part of Springer Nature.

Entities:  

Keywords:  Aldehydes; Fukuyama coupling; Fukuyama reduction; Fukuyama–Mitsunobu alkylation; Thioesters

Mesh:

Substances:

Year:  2021        PMID: 33575984     DOI: 10.1007/s11030-021-10194-7

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  36 in total

1.  Solid-phase synthesis of amine-bridged cyclic enkephalin analogues via on-resin cyclization utilizing the Fukuyama-Mitsunobu reaction.

Authors:  Yosup Rew; Murray Goodman
Journal:  J Org Chem       Date:  2002-12-13       Impact factor: 4.354

2.  Total synthesis of (+)-yatakemycin.

Authors:  Kentaro Okano; Hidetoshi Tokuyama; Tohru Fukuyama
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

Review 3.  Synthetic applications and methodology development of Chan-Lam coupling: a review.

Authors:  Iqra Munir; Ameer Fawad Zahoor; Nasir Rasool; Syed Ali Raza Naqvi; Khalid Mahmood Zia; Raheel Ahmad
Journal:  Mol Divers       Date:  2018-08-30       Impact factor: 2.943

4.  Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues.

Authors:  M Kambe; E Arai; M Suzuki; H Tokuyama; T Fukuyama
Journal:  Org Lett       Date:  2001-08-09       Impact factor: 6.005

5.  Pd(OH)2/C (Pearlman's catalyst): a highly active catalyst for Fukuyama, Sonogashira, and Suzuki coupling reactions.

Authors:  Yoshikazu Mori; Masahiko Seki
Journal:  J Org Chem       Date:  2003-02-21       Impact factor: 4.354

6.  Stereocontrolled total synthesis of (-)-ephedradine A (orantine).

Authors:  Wataru Kurosawa; Toshiyuki Kan; Tohru Fukuyama
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

7.  Total synthesis and structural revision of the marine macrolide neopeltolide.

Authors:  Daniel W Custar; Thomas P Zabawa; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

8.  The smallest and one of the brightest. Efficient preparation and optical description of the parent borondipyrromethene system.

Authors:  Ismael J Arroyo; Rongrong Hu; Gabriel Merino; Ben Zhong Tang; Eduardo Peña-Cabrera
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

9.  Cytotoxic compounds from a two-sponge association.

Authors:  J H Jung; C J Sim; C O Lee
Journal:  J Nat Prod       Date:  1995-11       Impact factor: 4.050

10.  Total synthesis and biological activity of neopeltolide and analogues.

Authors:  Viktor V Vintonyak; Brigitte Kunze; Florenz Sasse; Martin E Maier
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

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