Asymmetric synthesis of β-hydroxy sulfones by reduction of chiral β-keto sulfones

Bernabeu, Melania; Bonete, Pedro; Caturla, Francisco; Chinchílla, Rafael; Nájera, Carmén

doi:10.1016/0957-4166(96)00310-2

Cited by 22 publications

(6 citation statements)

References 15 publications

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“…An early reduction method to synthesize β‐substituted chiral sulfones were reported by Najera's group in 1996 (Scheme 22). [38] The various chiral sulfones 44 could be obtained by enantiospecific reduction of ketosulfones 43 using various metal hydrides, and the products of opposite configurations were obtained with good yields (52–100 %) and high selectivity (10 : 99–90 : 10 R/S ) when DIBAL‐H or LiAlH 4 as reducing agent, the authors proposed two different transition states TS‐7 and TS‐8 to explain this interesting phenomenon.…”

Section: Synthesis Of Sulfone‐containing Chiral Open‐chain Compoundsmentioning

confidence: 99%

Recent Progress on the Synthesis of Chiral Sulfones

Huang

Chen

et al. 2021

The Chemical Record

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Chiral sulfones extensively exist in drugs, agricultural chemicals, chiral organic intermediates, and functional materials. Their importance causes the rapid development of their synthetic methods in recent years. Many transition metal complex catalysts with chiral ligands and chiral organocatalysts are adopted in synthesis of chiral sulfones. Most of the methods to construct chiral sulfones are based on the reduction of unsaturated sulfones and the introduction of sulfone groups into unsaturated hydrocarbons. This review describes all classes of asymmetric reactions for synthesis of chiral sulfones.

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Section: Synthesis Of Sulfone‐containing Chiral Open‐chain Compoundsmentioning

confidence: 99%

Recent Progress on the Synthesis of Chiral Sulfones

Huang

Chen

et al. 2021

The Chemical Record

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“…Chiral hydroxysulfides serve as important intermediates in the synthesis of naturally occurring spiroketal pheromones,45 chiral oxiranes,32,46,47 thiiranes,48 tetrahydrofurans49,50 and 4‐acetoxyazetidinones 51. Furthermore, they are readily transformed into hydroxysulfoxides52–54 or sulfones,55 which are valuable building blocks in the synthesis of natural products.…”

Section: Baker's‐yeast‐mediated Resolution Of Keto Sulfidesmentioning

confidence: 99%

Baker's‐Yeast‐Mediated Reduction of Sulfur‐Containing Compounds

Deasy

Maguire

2014

Eur J Org Chem

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Both the efficiency and the stereoselectivity in baker's‐yeast‐mediated reduction of ketones are strongly influenced by both the presence and the position of sulfur substituents, or indeed by the use of sulfur‐containing additives. Interestingly the oxidation level of the sulfur substituent has a powerful impact on the outcome of the yeast reduction. It is apparent that use of the sulfone moiety as a substituent to influence the efficiency and stereoselectivity in ketone reduction is substantially more effective than use of the analogous sulfide and sulfoxide moieties.

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“…3 In 1996, Nájera and co-workers described 1,6-remote asymmetric induction in hydride addition to a prochiral carbonyl function separated from the inducing stereogenic centre by a π-aryl moiety. 37 1,6-Asymmetric reduction of a chiral β-keto sulfone 57 derived from (R)-N-α-methylbenzylamine was Transition states 58 and 60 were proposed to explain the stereoselectivity of the reductions. In the case of the LiAlH 4 reduction, a chair-like transition state 58 was suggested in which the lithium cation is on the same side as the methyl group of the stereogenic centre.…”

Section: Transfer Of Chirality Via a -Aryl Systemmentioning

confidence: 99%