Highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and sulfides.
نویسندگان
چکیده
A highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and allyl and propargyl sulfides by a double asymmetric induction approach that combines a chiral camphor sultam auxiliary and Cu(I) catalyst with chiral or achiral diimine ligands has been developed.
منابع مشابه
Catalytic asymmetric [2,3]-sigmatropic rearrangement of sulfur ylides generated from copper(I) carbenoids and allyl sulfides.
Catalytic asymmetric sulfur ylide [2,3]-sigmatropic rearrangement of carbenoids generated from aryldiazoacetates has been investigated with a number of chiral Rh(II) and Cu(I) catalysts, and moderately high enantioselectivity (52-78% ee) can be achieved with Cu(MeCN)(4)PF(6)/2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline].
متن کاملHighly efficient [2,3]-sigmatropic rearrangement of sulfur ylide derived from Rh(II) carbene and sulfides in water
Introduction Since their discovery in the late 1960s, the [2,3]-sigmatropic rearrangements of sulfonium ylides have received considerable attention because of their applications in organic synthesis and their probable involvement in biochemical processes. The most common method for sulfonium ylide generation involves the removal of a proton from a sulfonium salt with a strong base. However, a m...
متن کاملCatalytic asymmetric [2,3] sigmatropic rearrangement of sulfur ylides generated from carbenoids and propargyl sulfides
Catalytic asymmetric [2,3] sigmatropic rearrangement of sulfur ylides generated from aryldiazoacetates and propargyl sulfides with a number of chiral Rh(II) and Cu(I) catalysts have been investigated and moderately high enantioselectivities (up to 81% ee) have been achieved. © 2003 Elsevier Science Ltd. All rights reserved.
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Stereoselective synthesis of a cyclopentane nucleus by convergent annulation constitutes a significant challenge for synthetic chemists. Although a number of biologically relevant cyclopentane natural products are known, more often than not, the cyclopentane core is assembled in a stepwise manner because of the lack of efficient annulation strategies. Here we report the rhodium-catalysed reacti...
متن کاملA gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides.
An efficient C-O, C-S and C-C bond-forming sequence leads to functionalised compounds bearing sulfur-substituted quaternary carbons. Ynamides are employed as diazo-equivalents to access the [2,3]-sigmatropic rearrangements of allyl sulfonium ylides by a three-component chemoselective oxidation and intermolecular ylide formation.
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ورودعنوان ژورنال:
- Journal of the American Chemical Society
دوره 127 43 شماره
صفحات -
تاریخ انتشار 2005