(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates

Berg, C. Annette; Eichenauer, Nils C.; Pietruszka, Jörg

doi:10.1351/pac-con-12-03-04

Cited by 20 publications

(9 citation statements)

References 184 publications

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“…One drawback of allylboronates, described by Hoffmann et al,3 is the difficulty in their purification. To avoid this problem, we introduced diol 1 4 (Scheme ) as the protecting group of choice, providing boronates with increased stability 2f. This diol has been used to synthesise a variety of allylboronate reagents containing a stereogenic center in the position α to the boron moiety 5.…”

Section: Introductionmentioning

confidence: 99%

Importance of the Support Properties for Immobilization or Purification of Enzymes

et al. 2015

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Immobilization and purification of enzymes are usual requirements for their industrial use. Both purification and immobilization have a common factor: they use a solid activated support. Using a support for enzyme purification means having mild conditions for enzyme release and a selective enzyme–support interaction is interesting. When using a support for immobilization, however, enzyme desorption is a problem. The improvement of enzyme features through immobilization is a usual objective (e.g., stability, selectivity). Thus, a support designed for enzyme purification and a support designed for enzyme immobilization may differ significantly. In this review, we will focus our attention on the requirements of a support surface to produce the desired objectives. The ideal physical properties of the matrix, the properties of the introduced reactive groups, the best surface activation degree to reach the desired objective, and the properties of the reactive groups will be discussed.

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Section: Introductionmentioning

confidence: 99%

Importance of the Support Properties for Immobilization or Purification of Enzymes

et al. 2015

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“…Despite the dramatic improvement of the sequence, there are still drawbacks that need addressing: a) The synthesis of diol 7 is step intensive; b) The reaction rates for allyl additions are relatively low and in some cases reaction times >7 days are necessary; c) Both γ‐products 6 and dia ‐ 6 form predominantly the Z ‐homoallylic alcohols, while the corresponding E compounds cannot be obtained. Tartrate 13 / 14 based bisboronate 15 might be an alternative (Scheme )…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Catalysts for the Synthesis of α‐Substituted Allylboronates—An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols

et al. 2015

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The use of a convenient protecting group for boronates allows a selective, catalyzed S(N)2' reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.

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“…An account discussing the use of (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol (Pietruszka's chiral auxiliary) as a chiral auxiliary in various asymmetric reactions (including the cyclopropanation of alkenyl boronates) was published by Pietruszka and co-workers in 2012. 43 Imai and co-workers reported asymmetric cyclopropanation of (+)-diisopropyl tartrate (DIPT)-derived alkenylboronic esters 30 (R = alkyl, Ph) that relied on the use of the Simmons-Smith reagent from 3 equivalents of CH 2 I 2 and large excess of Zn-Cu couple (Scheme 11). 44 Deng and co-workers performed successfully the cyclopropanation of (E)-styrylboronate 32 derived from (+)-N,N,N′N′-tetramethyltartaric acid diamide (TMTA) 45 (Scheme 12).…”

Section: Scheme 10 Ch 2 N 2 -Mediated Cyclopropanation Of Alkenyl Bormentioning

confidence: 99%

Cycloadditions of Alkenylboronic Derivatives

et al. 2020

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

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(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates

Cited by 20 publications

References 184 publications

Importance of the Support Properties for Immobilization or Purification of Enzymes

Importance of the Support Properties for Immobilization or Purification of Enzymes

Enantioselective Catalysts for the Synthesis of α‐Substituted Allylboronates—An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols

Cycloadditions of Alkenylboronic Derivatives

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