Thiosilanes, a promising class of reagents for selective carbonyl protection

Evans, David A.; Truesdale, Larry K.; Grimm, Kurt; Nesbitt, Stephen L.

doi:10.1021/ja00457a020

Cited by 180 publications

(70 citation statements)

References 10 publications

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“…Besides organosilanes, organosulfur derivatives of silanes can also be used to protect carbonyl groups selectively [22]. However, methods of their preparation require air-sensitive catalysts such as B(C 6 H 5 ) 3 [23], and in some cases, sulphur poisoning is observed leading to much lower efficiency achieved in the catalytic system [24].…”

Section: Introductionmentioning

confidence: 99%

Ruthenium carbonyl-catalysed Si–heteroatom X coupling (X = S, O, N)

Toh

Poh

Lim

et al. 2012

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

Ruthenium carbonyl-catalysed Si–heteroatom X coupling (X = S, O, N)

Toh

Poh

Lim

et al. 2012

Journal of Organometallic Chemistry

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“…However, bis[(trimethylsilyl)thio]ethane and catalytic trimethylsilyl triflate were used for thioketal formation under mild conditions. [38] Upon treatment of the crude thioketal with Raney Ni, the desired deoxygenated product 36 was isolated.…”

Section: /Kap1mentioning

confidence: 99%

The Frondosins: An Unusual Synthetic and Stereochemical Journey

VanHeyst

Wright

2014

Eur J Org Chem

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Isolated from the marine sponge Dysidea frondosa, the frondosin family of meroterpenoid natural products were shown to be antagonists of the binding of the cytokine interleukin‐8 to its receptor. With implications of interleukin‐8 management being associated with a wide range of acute and chronic inflammatory disorders, as well as tumor progression and/or metathesis, there have been a multitude of syntheses of these natural products in the hopes of developinging new pharmacological agents. However, assignment of the absolute configurations of these natural products became unclear, because the first two syntheses of frondosin B, by Danishefsky and by Trauner, produced conflicting assignments for the single stereogenic center at C8. Here we describe the initial stereochemical mystery surrounding the Danishefsky and Trauner syntheses and provide evidence through ensuing syntheses of frondosins B and A that resolve this issue. These subsequent asymmetric syntheses have established that (1) the natural product occurs as the R enantiomer, and (2) a late‐stage stereochemical inversion occurred during the Trauner and Wright syntheses of frondosin B.

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“…Usually, they are prepared via the condensation of carbonyl compounds with thiols in the presence of protic acids or Lewis acids, such as ZnCl 2 , 3 NiCl 2 , 4 InCl 3 , 5 I 2 , 6 NBS 7 and SiO 2 -SO 3 H. 8 Herein, we wish to report a vicinal acyloxy group participation S N 2 reaction of ethanethiol under the standard thioacetalization conditions.…”

Section: Introductionmentioning

confidence: 99%

A Vicinal Acyloxy Group Participation S_N2 Reaction of Thiol Nucleophiles in the Formation of Thioacetals

Wu¹,

Chen

et al. 2009

Chin. J. Chem.

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Thioacetalization of acyl protected furanosides led to products with an ethanethiol group at C-2 and 3-O-acetyl-1,2-di-O-isopropylidene-D-furanoses were converted into corresponding thioacetals with two ethanethiol groups at both C-2 and C-3 positions under the standard thioacetalization conditions. All products were characterized by 1 H NMR, 13 C NMR and HRMS data. X-ray structure analysis indicates that the vicinal acyloxy group is stereoselectively substituted by ethanethiols. The supposed mechanisms for these two kinds of transformations were presented.

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Thiosilanes, a promising class of reagents for selective carbonyl protection

Cited by 180 publications

References 10 publications

Ruthenium carbonyl-catalysed Si–heteroatom X coupling (X = S, O, N)

Ruthenium carbonyl-catalysed Si–heteroatom X coupling (X = S, O, N)

The Frondosins: An Unusual Synthetic and Stereochemical Journey

A Vicinal Acyloxy Group Participation S_N2 Reaction of Thiol Nucleophiles in the Formation of Thioacetals

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Thiosilanes, a promising class of reagents for selective carbonyl protection

Cited by 180 publications

References 10 publications

Ruthenium carbonyl-catalysed Si–heteroatom X coupling (X = S, O, N)

Ruthenium carbonyl-catalysed Si–heteroatom X coupling (X = S, O, N)

The Frondosins: An Unusual Synthetic and Stereochemical Journey

A Vicinal Acyloxy Group Participation SN2 Reaction of Thiol Nucleophiles in the Formation of Thioacetals

Contact Info

Product

Resources

About

A Vicinal Acyloxy Group Participation S_N2 Reaction of Thiol Nucleophiles in the Formation of Thioacetals