2012
DOI: 10.1126/science.1229208
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Abstract: Progress in the development of asymmetric Heck couplings of arenes and acyclic olefins has been limited by a tenuous understanding of the factors that dictate selectivity in migratory insertion and β-hydride elimination. On the basis of key mechanistic insight recently garnered in the exploration of selective Heck reactions, we report here an enantioselective variant that delivers β-, γ-, or δ-aryl carbonyl products from acyclic alkenol substrates. The catalyst system imparts notable regioselectivity during mi… Show more

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Cited by 409 publications
(244 citation statements)
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References 50 publications
(38 reference statements)
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“…Author Manuscript alcohols using aryldiazonium salts, [3] arylboronic acids, [4] and alkenyl triflates, [5] which provides direct preparation of carbonyl compounds that contain remote alkenyl/aryl stereocenters (Scheme 1A). However, this emerging strategy has thus far been limited to sp 2 -hybridized nucleophiles/electrophiles as coupling partners.…”
Section: Author Manuscript Author Manuscriptmentioning
confidence: 99%
See 1 more Smart Citation
“…Author Manuscript alcohols using aryldiazonium salts, [3] arylboronic acids, [4] and alkenyl triflates, [5] which provides direct preparation of carbonyl compounds that contain remote alkenyl/aryl stereocenters (Scheme 1A). However, this emerging strategy has thus far been limited to sp 2 -hybridized nucleophiles/electrophiles as coupling partners.…”
Section: Author Manuscript Author Manuscriptmentioning
confidence: 99%
“…[3] In addition, no significant change was observed when the reaction temperature was decreased to 15 °C (entry 6). Surprisingly, switching to a Pd(0) precatalyst (Pd 2 (dba) 3 ) resulted in <5% product formation (entry 7). In contrast, Buchwald's precatalyst, known to form Pd(0) in situ upon heating or adding base, [12] furnished the desired product (2a) in 65% yield and 96:4 er.…”
mentioning
confidence: 98%
“…31,32 Distinct from the above-described approach, Sigman and co-workers have recently reported a Pd-catalyzed enantioselective redox-relay Heck reaction of acyclic alkenyl 1°and 2°a lcohols where aryl addition is followed by olefin migration through the carbon chain and eventually oxidation of the alcohol. 33 The authors capitalized on previous works which described similar outcome when allylic alcohols were employed. 34 Key to the success of this approach was the use of an electrophilic catalyst which favoured migration (i.e.…”
Section: Heck-typementioning
confidence: 99%
“…1 There are very few reports describing this enantioselective reaction. 2,3 Because of the great interest in the synthesis of chiral compounds, new enantioselective methods are welcome. Since the first example of the enantioselective Heck-Matsuda reaction was reported, 2 the Correia's group has been intensely studying this reaction.…”
Section: Introductionmentioning
confidence: 99%