Literature DB >> 35548924

Diastereoselective additions of H-phosphinates to alkenyl ketones under phase-transfer conditions.

Krishna P Yadavalli1, Johannah E Cummines1, Chace J Carlisle1, Salvatore D Lepore1.   

Abstract

Additions of bulky H-phosphinates to β,β-disubstituted alkenyl ketones under the action of a phase transfer-catalyst led to a new class of carbon quaternary center-containing phosphinates with unprecedented control of the relative configuration of the adjacent carbon and phosphorous chiral centers with high diastereoselectivity in most cases.

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Year:  2022        PMID: 35548924      PMCID: PMC9365031          DOI: 10.1039/d2cc02090d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.065


  12 in total

1.  Enantioselective organocatalytic phospha-Michael reaction of alpha,beta-unsaturated ketones.

Authors:  Shigang Wen; Pengfei Li; Haibo Wu; Feng Yu; Xinmiao Liang; Jinxing Ye
Journal:  Chem Commun (Camb)       Date:  2010-05-25       Impact factor: 6.222

2.  Triple-helical transition state analogues: a new class of selective matrix metalloproteinase inhibitors.

Authors:  Janelle Lauer-Fields; Keith Brew; John K Whitehead; Shunzi Li; Robert P Hammer; Gregg B Fields
Journal:  J Am Chem Soc       Date:  2007-08-02       Impact factor: 15.419

3.  P(═O)H to P-OH Tautomerism: A Theoretical and Experimental Study.

Authors:  Benjamin G Janesko; Henry C Fisher; Mark J Bridle; Jean-Luc Montchamp
Journal:  J Org Chem       Date:  2015-09-29       Impact factor: 4.354

4.  Diastereoselective synthesis of P-stereogenic heterocycles via enyne ring-closing metathesis.

Authors:  James Stephen Harvey; Guy T Giuffredi; Véronique Gouverneur
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

5.  Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.

Authors:  Artur Mucha; Paweł Kafarski; Łukasz Berlicki
Journal:  J Med Chem       Date:  2011-08-05       Impact factor: 7.446

Review 6.  Synthesis of beta-aminophosphonates and -phosphinates.

Authors:  Francisco Palacios; Concepción Alonso; Jesús M de Los Santos
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

7.  Diastereoselective synthesis of alpha,beta'-disubstituted aminomethyl(2-carboxyethyl)phosphinates as phosphinyl dipeptide isosteres.

Authors:  Takehiro Yamagishi; Hiroyuki Ichikawa; Terumitsu Haruki; Tsutomu Yokomatsu
Journal:  Org Lett       Date:  2008-09-10       Impact factor: 6.005

8.  Stereospecific nucleophilic substitution of optically pure H-phosphinates: a general way for the preparation of chiral P-stereogenic phosphine oxides.

Authors:  Qing Xu; Chang-Qiu Zhao; Li-Biao Han
Journal:  J Am Chem Soc       Date:  2008-08-30       Impact factor: 15.419

Review 9.  Phosphinate-containing heterocycles: A mini-review.

Authors:  Olivier Berger; Jean-Luc Montchamp
Journal:  Beilstein J Org Chem       Date:  2014-03-27       Impact factor: 2.883

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