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Literature DB >> 19341239

A method for the preparation of differentiated trans-1,2-diol derivatives with enantio- and diastereocontrol.

Sang Min Lim¹, Nicholas Hill, Andrew G Myers.

Abstract

We describe a synthetic sequence that allows for the preparation of optically active trans-1,2-diol monosilyl ether derivatives from ketones, providing a new means for retrosynthetic simplification of differentiated diol and polyol targets. The sequence involves silyl enol ether formation, Shi asymmetric epoxidation, and then regio- and stereospecific addition of hydride, methide, or higher alkylide. The tactical combination presented has not been integrated in synthetic problem solving, so far as we are aware, but has promise for broad application.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19341239 PMCID： PMC2681323 DOI： 10.1021/ja901283q

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

5 in total

1. Total synthesis and structure assignment of the anthrone C-glycoside cassialoin.

Authors: Yasuhito Koyama; Ryo Yamaguchi; Keisuke Suzuki
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Aluminum- and boron-mediated c-glycoside synthesis from 1,2-anhydroglycosides.

Authors: J D Rainier; J M Cox
Journal: Org Lett Date: 2000-08-24 Impact factor: 6.005

3. Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes.

Authors: Paschalis Dimopoulos; Jonathan George; Derek A Tocher; Soraya Manaviazar; Karl J Hale
Journal: Org Lett Date: 2005-11-24 Impact factor: 6.005

4. Transition state studies on the dioxirane-mediated asymmetric epoxidation via kinetic resolution and desymmetrization.

Authors: Jon C Lorenz; Michael Frohn; Xiaoming Zhou; Jian-Rong Zhang; Yong Tang; Christopher Burke; Yian Shi
Journal: J Org Chem Date: 2005-04-15 Impact factor: 4.354

5. Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Authors: Yian Shi
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

5 in total

9 in total

1. Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Alkene Isomerizations and Diene Metalations.

Authors: Russell F Algera; Yun Ma; David B Collum
Journal: J Am Chem Soc Date: 2017-08-14 Impact factor: 15.419

2. Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins.

Authors: Paul E Gormisky; M Christina White
Journal: J Am Chem Soc Date: 2011-07-27 Impact factor: 15.419

3. Simple strategy for synthesis of optically active allylic alcohols and amines by using enantioselective organocatalysis.

Authors: Hao Jiang; Nicole Holub; Karl Anker Jørgensen
Journal: Proc Natl Acad Sci U S A Date: 2010-06-14 Impact factor: 11.205

9. Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic syn- or anti-1,2-Diols from Aldehydes and Dienol Ethers.

Authors: Thomas Q Davies; John J Murphy; Maxime Dousset; Alois Fürstner
Journal: J Am Chem Soc Date: 2021-08-19 Impact factor: 15.419

9 in total

A method for the preparation of differentiated trans-1,2-diol derivatives with enantio- and diastereocontrol.

1. Total synthesis and structure assignment of the anthrone C-glycoside cassialoin.

2. Aluminum- and boron-mediated c-glycoside synthesis from 1,2-anhydroglycosides.

3. Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes.

4. Transition state studies on the dioxirane-mediated asymmetric epoxidation via kinetic resolution and desymmetrization.

5. Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

1. Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Alkene Isomerizations and Diene Metalations.

2. Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins.

3. Simple strategy for synthesis of optically active allylic alcohols and amines by using enantioselective organocatalysis.

4. Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

5. Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.

6. Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols.

7. Synthesis and Biological Evaluation of Kibdelone C and Its Simplified Derivatives.

Review 8. Polycyclic xanthone natural products: structure, biological activity and chemical synthesis.

9. Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic syn- or anti-1,2-Diols from Aldehydes and Dienol Ethers.