A selective reduction using tris(triphenylphosphine)-chlororhodium I

Brown, Morris; Piszkiewicz, L. W.

doi:10.1021/jo01281a079

Cited by 40 publications

(4 citation statements)

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“…Thus, we chose to hydrogenate the enone of scaffolds such as 13 . Comparison of nickel-, palladium-, rhodium-, and copper-based 19 catalysts showed no reactivity for reduction of substrate 13 . After considerable experimentation, we found that Adams' catalyst (PtO 2 ) gave promising results .…”

Section: Resultsmentioning

confidence: 97%

Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds

et al. 2005

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We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.

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Section: Resultsmentioning

confidence: 97%

Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds

et al. 2005

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“…The importance of an alkene reduction method that tolerated most other functional groups was immediately recognized by Birch and Walker and led to a series of papers that firmly established the scope of this new synthetic reaction (Scheme a) . Other early authors reinforced this contribution . It also proved to be a valuable resource for the site-specific introduction of deuterium or tritium by Rh complex catalyzed addition …”

Section: Introductionmentioning

confidence: 99%

Rhodium Asymmetric Hydrogenation Observed during its Exponential Growth Phase

Brown

2014

Organometallics

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The field of asymmetric hydrogenation grew rapidly after the early 1970s. What had begun as a demonstration of enantioselectivity in catalysis by purely chemical means became an important tool both for academic research and for industry. Right from the beginning, a question was posed as to how relatively simple catalysts were able to generate such unprecedented levels of stereoselectivity. This article provides an account of Oxford-based contributions to the field of rhodium complex catalyzed asymmetric hydrogenation from 1978 onward, when the initial realization of this practical catalytic method for synthesis of single enantiomers had already been achieved. NMR-based experiments that help to elucidate the structures of reactive intermediates in catalysis are strongly emphasized here and linked to the present understanding of the mechanism of a reaction that has sustained interest over the intervening years.

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“…To test this hypothesis, the terminal olefinic group of (+)-nootkatone (3) was selectively reduced utilizing Wilkinson's catalyst (entry 7). 15,16 The hydrogenation product, 11,12-dihydronootkatone (11), was subjected to both catalytic hydrogenation (entry 8) and transfer hydrogenation conditions (entry 9). Both methods provided the trans-isomer exclusively, implying that this recurring result was not a result of the isopropylidene's influence, but actually arose from the steric impact imparted by the C-4 methyl substituent.…”

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confidence: 99%