1989
DOI: 10.1021/ja00191a049
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Abstract: We report here novel catalytic asymmetric synthesis of optically active 1-arylalkanols (up to 96% ee) through asymmetric hydroboration of styrenes catalyzed by a chiral cationic rhodium complex, which complements the uncatalyzed asymmetric hydroboration with chiral alkylboranes derived from -pinene that has been successfully used for internal alkenes.1,2Since Mannig and Noth reported in 1985 that rhodium complexes catalyze the hydroboration with catecholborane,3 a few reports have appeared on application of th… Show more

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Cited by 260 publications
(117 citation statements)
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“…[116] Impressive enantioselectivities were obtained and the sterically demanding cyclic substrates were hydroborated in 64 -84% ee, entries 23 and 24, as well as b-substituted vinylarene (E)-30 with a similar enantioselectivity as with QUINAP (82). Com- pared to the corresponding results obtained with diphosphine ligands, Section 4, it is clear that QUINAP (82), its structural relatives 83 -86 and PHENAP (87), give superior results in the asymmetric rhodium-catalysed hydroboration of several vinylarenes, and are essentially the only practical solution for b-substituted alkenes. [117] The reasons for this are not well understood, but are thought to be due to the particular geometry of the P,N chelate which can accommodate the steric demand of substituents in the region of the alkene double bond.…”
Section: Axial Chiralitymentioning
confidence: 67%
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“…[116] Impressive enantioselectivities were obtained and the sterically demanding cyclic substrates were hydroborated in 64 -84% ee, entries 23 and 24, as well as b-substituted vinylarene (E)-30 with a similar enantioselectivity as with QUINAP (82). Com- pared to the corresponding results obtained with diphosphine ligands, Section 4, it is clear that QUINAP (82), its structural relatives 83 -86 and PHENAP (87), give superior results in the asymmetric rhodium-catalysed hydroboration of several vinylarenes, and are essentially the only practical solution for b-substituted alkenes. [117] The reasons for this are not well understood, but are thought to be due to the particular geometry of the P,N chelate which can accommodate the steric demand of substituents in the region of the alkene double bond.…”
Section: Axial Chiralitymentioning
confidence: 67%
“…However, increasing the phosphine-to-rhodium ratio from 1 : 1 to 2 : 1 for the same ligand caused a complete reversal of the regioselectivity to 8 : 1 in favour of the Markovnikov product 46, entry 6, approaching the near complete regioselectivities previously observed by Hayashi in the rhodium-catalysed hydroboration of vinylarenes. [11,87] "Asymmetric amplification" experiments provided no evidence to suggest there was more than one phosphine ligand per catalyst molecule but did not conclusively rule out that possibility either. [94] Subsequently, Burgess [95] prepared a series of hybrid ligands 51 -53, Figure 5, which were chiral not only in the carbon backbone like (R,R)-DIOP (24), but also at phosphorus, like DIPAMP (50).…”
Section: Chiral Pp Ligandsmentioning
confidence: 98%
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