A New Asymmetric Synthesis of (<i>R</i>)- and (<i>S</i>)-3-Arylphthalides: Extremely High Diastereoselective Reaction of Arylcarbaldehydes with Chiral [2-(1,3-Oxazolidin-2-yl)phenyl]titanium Ate Complexes

Takahashi, Hiroshi; Tsubuki, Takeshi; Higashiyama, Kimio

doi:10.1055/s-1992-26199

Cited by 21 publications

(6 citation statements)

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“…It is known that isobenzofuranones are particularly useful materials as synthetic intermediates. 16, 17 The present reaction provides a useful synthesis of isobenzofuranones as well as insight into the photochemistry of thioesters.…”

Section: Resultsmentioning

confidence: 94%

Photochemical transformation of S-aryl 2-benzoylbenzothioates to 3-phenyl-3-arylthiobenzofuranones involving aryl migration

Takahashi¹,

Fujita²,

Watanabe³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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Section: Resultsmentioning

confidence: 94%

Photochemical transformation of S-aryl 2-benzoylbenzothioates to 3-phenyl-3-arylthiobenzofuranones involving aryl migration

Takahashi¹,

Fujita²,

Watanabe³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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“…In an analogous strategy, a titanium complex is used for the synthesis of 3-arylphthalides. Chiral [2-(1,3-oxazolidin-2-yl)phenyl]-titanium complexes 287 , derived from corresponding lithio derivatives 286 , on reaction with aryl aldehydes gave 288 (Scheme ).…”

Section: Phthalidesmentioning

confidence: 99%

“…107 Thus, lithium−bromine exchange of 280 with t-BuLi followed by quenching with benzaldehyde gave a mixture of diastereomers 281 and 282 in a 2. In an analogous strategy, 108 a titanium complex is used for the synthesis of 3-arylphthalides. Chiral [2-(1,3-oxazolidin-2yl)phenyl]-titanium complexes 287, derived from corresponding lithio derivatives 286, on reaction with aryl aldehydes gave 288 (Scheme 65).…”

Section: Table 1 Structurally Analogous Natural Productsmentioning

confidence: 99%

Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis

2014

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Scheme 10. Schmalz Synthesis of 3-Substituted Phthalides from 2-Formylketones Scheme 11. Enantioselective Synthesis of Phthalides via Ketone Hydroacylation Scheme 12. Synthesis of 3-Alkylphthalides from Sulfonylmethyl Benzoic Acids Scheme 13. Synthesis of an Isobenzofuranone via Thermolysis of a Bromomethylbenzoate Scheme 14. Kraus Approach to 3-Cyanophthalide Scheme 15. Ohzeki and Mori Synthesis of (−)-3-Butyl-7hydroxyphthalide Scheme 16. Asymmetric Dihydroxylation-Lactonization Route to Phthalides Chemical Reviews Review dx.

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“…It has been postulated that cheap ( i -PrO) 4 Ti can be used to generate Li or Mg M,Ti-heteroMAAs, also called titanates, at low temperatures, for example, by reaction with MeLi, dihalomethyllithiums, allyllithiums, allylMgCl, functionalized phenyllithiums, and Li enolates …”

Section: Formation and Main Features Of Maasmentioning

confidence: 99%

Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs

2013

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6. Conclusion 7706 Author Information 7706 Biographies 7707 Acknowledgment 7707 Abbreviations Used 7707 References 7708the corresponding allyl-and propargylchromium reagents that further react with a variety of electrophiles to afford the corresponding adducts in high yields. 102 Bu 6 CrLi 3 similarly behaves as a formal two-electron reductant with ketones and esters bearing a leaving group at the α-position to produce enolates that are intercepted with a variety of electrophiles with high selectivities (Table 8). 103 Such enolates are also capable of reacting with oxiranes to afford γand β-hydroxy esters, depending on the Lewis acid used as promoter. 2143.2.2. Two-Electron Transfers from M,Mn-HeteroMAAs (M = Li, MgX). In 1976, Cahiez et al. disclosed the possible reduction in THF of alkenyl bromides or iodides, as well as aryl chlorides or bromides, using i-PrMgCl in the presence of a catalytic amount of MnCl 2 . 215 The authors proposed the in situ formation of unstable i-Pr 3 MnMgCl and its decomposition by β-elimination to H 3 MnMgCl; reaction of the latter with the halide would then afford an unstable Mn(IV) intermediate, able Scheme 23 Scheme 24 Scheme 21 Scheme 22

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A New Asymmetric Synthesis of (R)- and (S)-3-Arylphthalides: Extremely High Diastereoselective Reaction of Arylcarbaldehydes with Chiral [2-(1,3-Oxazolidin-2-yl)phenyl]titanium Ate Complexes

Cited by 21 publications

References 0 publications

Photochemical transformation of S-aryl 2-benzoylbenzothioates to 3-phenyl-3-arylthiobenzofuranones involving aryl migration

Photochemical transformation of S-aryl 2-benzoylbenzothioates to 3-phenyl-3-arylthiobenzofuranones involving aryl migration

Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis

Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs

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