Conversion of Torgov's Synthesis of Estrone into a Highly Enantioselective and Efficient Process

Yeung, Ying‐Yeung; Chein, Rong‐Jie; Corey, E. J.

doi:10.1021/ja0742434

Cited by 126 publications

(63 citation statements)

References 7 publications

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“…The tricyclic adduct was transformed in three highyielding steps to the keto aldehyde 22 which underwent addition/isomerization to form the tetracyclic dienone 23. (+)-Estrone is available from 23 by a one-flask procedure [17] in high yield. The second route to (+)-estrone, which is shorter still, is summarized in Scheme 6.…”

Section: New Synthesis Of Estronementioning

confidence: 99%

Enantioselective Catalysis Based on Cationic Oxazaborolidines

2009

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Over the past several decades a revolution has occurred in chemistry that has essentially been unnoticed by those outside the field, even in other sciences. In brief, this includes the following: 1) our understanding of how chemical reactions occur, 2) our ability to invent new reactions, 3) our ability to utilize reactions that construct a vast assortment of useful or complicated molecules, and 4) our ability to apply chemical principles and knowledge to understand biological and medical problems. Within synthetic chemistry, a new science has been set in place beside the old, especially in terms of the control of absolute and relative stereochemistry and the creation of new types of useful catalysts that function in ways that were hitherto unimaginable. This Review deals with one aspect of such catalysis which has emerged only in the past six years: the generation and application of super-Lewis acidic chiral oxazaborolidinium ions for enantioselective catalysis. Progress in this area has encompassed the formation of such catalysts, the detailed pathways of the reactions that they control and accelerate, the reactions that they can promote, and the ways in which they can be applied to advantage.

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Section: New Synthesis Of Estronementioning

confidence: 99%

Enantioselective Catalysis Based on Cationic Oxazaborolidines

2009

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“…[14] Structures bearing the amino alcohol motif have been employed as ligands for metal catalysts in various asymmetric additions to aldehydes. Enantiopure amino alcohols have been extensively used in synthesis as exemplified by Corey and co-workers, who used proline derivatives to form oxazaborolidine compounds 3 (Figure 2), [15] which were subse- …”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Methodology for the Direct Oxyamination of Olefins

Donohoe

Callens

Flores

et al. 2010

Chemistry A European J

267

116

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1,2-Amino alcohols are high-value, versatile functional groups that are found in scores of biologically active molecules and other interesting synthetic targets such as ligands and auxiliaries. Given their prominent position within organic compounds of import, it is no surprise to note that many routes have been developed to access this motif and there are many different starting points from which a synthetic chemist might embark on a synthesis. However, one particular approach stands out from the others, and this is the direct conversion of an alkene to a vicinal amino alcohol derivative (oxyamination). Research in this field has been particularly active in recent years and many interesting new methodologies have been reported. The purpose of this review is to give the reader a tour of the methods that have emerged in the last few years so one can appreciate the myriad of different metals and reagents that can accomplish the oxyamination of alkenes. There are still many challenges to be overcome and, herein, we also outline the areas that are ripe for further development and which bode well for the future.

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“…The Corey group has utilized these catalysts for a number of natural product synthesis, including estrone [35,36], desogestrel [35], oseltamivir (Tamiflu) [37], dolabellatrienone and dolabellatriene [38], aflatoxin B 2 [39], laurenditerpenol [40], and various others [41].…”

Section: Oxazaborolidine-based Catalystsmentioning

confidence: 99%

Bifunctional Acid Catalysts for Organic Synthesis

Yamamoto

2011

Bifunctional Molecular Catalysis

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The concept of bifunctional acid catalysis is very helpful for inventing new catalytic asymmetric reactions. Compared with single functional acid catalysts, cooperative effect of two acid components has the potential to fine tune the reactivity as well as the selectivity of desired reaction pathways. This chapter focuses on some representative examples on the recent developments of bifunctional acid catalysis, including combined acid catalysis and other cooperative acid catalysis.

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Conversion of Torgov's Synthesis of Estrone into a Highly Enantioselective and Efficient Process

Cited by 126 publications

References 7 publications

Enantioselective Catalysis Based on Cationic Oxazaborolidines

Enantioselective Catalysis Based on Cationic Oxazaborolidines

Recent Developments in Methodology for the Direct Oxyamination of Olefins

Bifunctional Acid Catalysts for Organic Synthesis

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