Novel stereospecific silyl group transfer reactions: practical routes to the prostaglandins

Danishefsky, Samuel J.; Cabal, María‐Paz; Chow, Ken

doi:10.1021/ja00191a067

Cited by 96 publications

(25 citation statements)

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“…[33] This high syn selectivity contrasts with the extremely high anti selectivity observed in the tris(diethylamino)sulfonium difluoromethylsilicate (TASF)-catalyzed reaction. The stereochemical reversal generally found in Lewis acid catalysis (for example, with HgI 2 ), [34] is explained in terms of stereoelectronic effects based on the Cieplak model. [35] OEt …”

Section: Diastereoselective Catalysis By Induced Stereochemical Fitmentioning

confidence: 97%

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“Asymmetric” Catalysis by Lanthanide Complexes

Mikami

Terada

Matsuzawa

2002

Angew. Chem. Int. Ed.

235

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velopment of asymmetric Ln catalysts, and their recyclable use, is of increasing importance. This review gives an overview of the most recent developments in catalysis with lanthanide(ii) and lanthanide(iii) complexes. REVIEWS[ + ] The elements specified in Figure 1 include scandium and yttrium, which are not formally defined as lanthanide elements, but as rare earth metals. For the sake of simplicity, in this review these two elements are also abbreviated to Ln.

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Section: Diastereoselective Catalysis By Induced Stereochemical Fitmentioning

confidence: 97%

“…This expectation is based on the elegant study by Corey on a catalytic process for the radical addition reaction by the use of 10 mol % of SmI 2 with Zn ± Hg, Me 3 SiOTf, and LiI [Eq. (34)]. [ …”

Section: Radical Addition Reactionsmentioning

confidence: 99%

“Asymmetric” Catalysis by Lanthanide Complexes

Mikami

Terada

Matsuzawa

2002

Angew. Chem. Int. Ed.

235

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“…These results demonstrate the potentiality of this method as a synthetic tool. 12 The reaction product isolated in tandem Michael imino aldol sequences involving enoxysilanes substituted with a tert-butyldimethylsilyl group is not a b-amino-substituted ketone, but the corresponding enoxysilane. 11d Similarly when the starting material is an enoxysilane substituted by a tert-butyldimethylsilyl group, samarium diiodide catalyzed imino aldol reactions result in tandem sequences because a second step involving the enolization of the bamino ketone occurs (Scheme 5).…”

Section: Methodsmentioning

confidence: 99%

Samarium Iodides: Catalysts for the Formation of Carbon-Nitrogen Bonds

Collin¹,

Bezzenine‐Lafollée²,

Gil³

et al. 2009

Synlett

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Lanthanide iodides offer great reactive scope as Lewis acid catalysts. Samarium diiodide allows a wide range of carboncarbon bond-forming reactions, such as Mukaiyama aldol, DielsAlder, or tandem Mukaiyama Michael aldol reactions. Moreover, lanthanide iodides exhibit high catalytic activities for carbon-nitrogen bond formations which are reviewed here. Highly enantioenriched amino alcohol and amino acid building blocks are obtained thanks to a new family of enantioselective catalysts developed in our laboratory, iodolanthanide binaphtholates.

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“…24 The chiral monoacetate ester is a key intermediate in the synthesis of a thromboxane A2 antagonist. Enzymatic hydrolysis of the (1a,2b,3a)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol diacetate has been demonstrated by Griffith and Danishefsky to produce the corresponding monoester using the acetylcholine esterase from the electric eel 25,26 and pocine pancreatic lipase by Legrand and Roberts. 27 An efficient synthesis of the carbocyclic nucleosides (À)-aristeromycin and (À)-neplanocin A has been developed in an enantioselective manner starting from the Diels-Alder adduct of cyclopentadiene and dimethyl acetylenedicarboxylate.…”

Section: Introductionmentioning

confidence: 99%