The First Highly Enantioselective Rh-Catalyzed Enyne Cycloisomerization

Cao, Ping; Zhang, X

doi:10.1002/1521-3773(20001117)39:22<4104::aid-anie4104>3.0.co;2-x

Cited by 128 publications

(43 citation statements)

References 28 publications

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“…( The cycloisomerization of 1,6-enynes can also be catalyzed enantioselectively using a Rh-BICP catalyst (eq 8). 15 However, Rh-Me-DuPhos affords a significantly higher enantioselectivity than Rh-BICP for this process ( Asymmetric Hydrogenation. A new catalyst system comprising Ru/L complexes in combination with inexpensive nonchiral 2-(alkylthio)amine or 1,2-diamine and an alkoxide as a base effects highly enantioselective hydrogenation of a variety of aryl ketones.…”

Section: Original Commentarymentioning

confidence: 99%

(1R,1′R,2R,2′R)-[1,1′-Bicyclopentyl-2,2′-diylbisdiphenylphosphine

Parquette

Nikonov

Likhareva

2014

Encyclopedia of Reagents for Organic Synthesis

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Section: Original Commentarymentioning

confidence: 99%

(1R,1′R,2R,2′R)-[1,1′-Bicyclopentyl-2,2′-diylbisdiphenylphosphine

Parquette

Nikonov

Likhareva

2014

Encyclopedia of Reagents for Organic Synthesis

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“…Two successful strategies, the enantioselective cycloisomerization (Scheme 9) and the auxiliary-based oxidative cyclodearomatization (Scheme 10) were employed to construct a single stereogenic center. In the former route, acetylinic ester (49) was prepared from intermediate (12) in four steps and subjected to rhodium(I)-catalyzed cyclization conditions [44,45], giving spirocyclic compound (50) in excellent yield and enantioselectively. Removal the undesired ester group gave the decarboxylation product (51) in five steps in moderate yield, which then subjected to the ketyl radical cyclization conditions as in the racemic synthesis (Scheme 3), leading to the key intermediate ((-)-6) in optically active form.…”

Section: Optically Active Formmentioning

confidence: 99%

Recent Advances on Platensimycin: A Potential Antimicrobial Agent

You²

2010

CMC

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Platensimycin, an active metabolite of Streptomyces platensis, was initially discovered by a combination of RNA interferin induced gene-silencing and library screening to microbial extracts. Platensimycin selectively inhibits beta - ketoacyl-acyl carrier protein (ACP) synthase II (FabF) that is recognized as an effective broad-spectrum antibiotic against drug-resistant microorganism strains. Its novel scaffold and extraordinary antibacterial activity have drawn great attentions in recent years. So far, a number of synthetic strategies have been explored for the total synthesis of platensimycin. Moreover, many analogues have been investigated in terms of structure-activity relationships (SAR). This review provides a detailed overview of updated studies on platensimycin, focusing on various total and formal synthetic strategies, development of analogues, and the structure-activity relationships.

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“…The role of the Ag additive was to generate an active cationic Rh species. Enantioselective rhodium-catalyzed cycloisomerization was also studied by utilizing chiral bidentate phosphine ligands [106]. A similar cycloisomerization using a combination of NiCl 2 (PPh 3 ) 2 and CrCl 2 catalysts was reported by Trost et al [107] (Scheme 1.80).…”

Section: Cycloisomerization Reactionsmentioning

confidence: 99%