Download PDF by Rainer Mahrwald: Aldol Reactions

Download PDF by Rainer Mahrwald: Aldol Reactions

By Rainer Mahrwald

ISBN-10: 1402087004

ISBN-13: 9781402087004

ISBN-10: 1402087012

ISBN-13: 9781402087011

Aldol Reactions offers a entire up to date evaluation of aldol reactions including:

  • Application of alternative steel enolates
  • Catalytic aldol additions catalyzed through diverse Lewis acids and Lewis bases
  • Enantioselective direct aldol additions
  • Antibodies and enzyme catalyzed aldol additions
  • The fresh competitive improvement of organocatalyzed aldol additions.

The energy of every strategy is proven by way of numerous purposes in overall synthesis of ordinary items. the professionals and cons of those methodologies with reference to stereoselectivity, regioselectivity and alertness in overall synthesis of usual items are mentioned. nice value is determined to the varied chances of the guide of aldol response to put in required configurations in complex usual product synthesis.

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LDA O 2. Ti(Oi-Pr)3Cl O 3. 4 Evans and coworkers used a combination of TiCl4 and i-Pr2NEt for syn-selective aldol addition. 5 For results with (S)-2-benzyloxy-3-pentanone in aldol additions under these conditions see Rodriguez-Cisterna et al. 6,7 R. V. 8 1. TiCl4, amine O 2. 10 Only a few examples of anti-selective titanium-mediated aldol additions have been published. 15 These results are consistent with those obtained in the lithium enolate series. 5. 5 Aldol additions of trisubstituted titanium enolates 42 2 Aldol Reactions with Preformed Enolates A further example of deployment of trisubstituted titanium enolates is the total synthesis of zaragozic acid.

The aldol addition proceeds via a chair-like, six-membered transition state, which is more rigid than those of alkali metal enolates. This is due to the shorter boron oxygen bond length, which guarantees a maximum of 1,3-diaxial interactions (R3 ↔ L) and thus the formation of the more stable transition states A and B. For that reason higher stereoselectivities were observed when used with boron enolates, compared to aldol additions of corresponding lithium enolates. The stereochemical outcome strongly depends on the geometry of the boron enolates used in these reactions.

2 Magnesium Enolates 21 Recently McNulty and coworkers have extended this method to the use of enolizable aldehydes. High anti-selectivities were detected in aldol additions of chiral auxiliary 13 with protected l-threose 12. Matched/mismatched situations were discussed by the use of both enantiomers of oxazolidinones. 30 The authors described difficulties during a Mukaiyama aldol step in the total synthesis of lactacystin. These problems could be overcome by the deployment of MgI2 in this Mukaiyama reaction step.

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Aldol Reactions by Rainer Mahrwald

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