Further improvement on sulfonamide-based ligand for catalytic asymmetric 2-haloallylation and allylation

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3073-3076

  Zhang, Zhiyu ^a   Huang, Jian ^a   Ma, Bin ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CHROMIUM; HALOGENATED HYDROCARBON; LIGAND; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALLYL COMPOUNDS; CATALYSIS; CHROMIUM; HYDROCARBONS, HALOGENATED; LIGANDS; MOLECULAR STRUCTURE; SULFONAMIDES;

EID: 52049109902     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801093p     Document Type: Article

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44. This ligand was synthesized as depicted below. For the details, see the Supporting Information. (Chemical Equation Presented)
45. 10 we attempted to synthesize 2,4,6-trimethylbenzylsulfonyl chloride, but unsuccessfully.
46. The tested conditions included: complexation at rt for 45 min, 1.5 h, and 2.5 h; complexation at 42°C for 45 min, 1.5 h, and 2.5 h. We attempted to follow the complexation event by react IR spectroscopy, but the result was not conclusive. Therefore, we relied on the overall performance (asymmetric induction and yield) of 2-haloallylation to draw this conclusion. We should note that, with this optimized complexation protocol, the reproducibility of 2-haloallylation was also improved.
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49. The catalyst loading was tested for the case of 2 + 4a → 7a; the following results were obtained: 10 mol % (yield = 85%, ee = 93%), 5 mol % (yield = 76%, ee = 92%), and 2.5 mol % (yield = 60%, ee = 91%).
50. The optical purity of 4b used was better than 99%.
51. 14
52. For the determination of absolute configuration, see Supporting Information of reference 1.
53. In the catalytic system, Cr(III) is reduced to Cr(II) by Mn in situ.
54. 3·3THF.
55. For a review on this subject, see: (a) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
56. 1H NMR analysis of its (+)-Mosher ester. Note: Large-scale 2-iodoallylation was carried out with the Pv- and TBDPS-protected aldehydes. The observed asymmetric induction was practically identical in the two series, but the yield in the TBDPS-series was 15-20% higher than that in the Pv series. In the TBDPS series, because of their similar polarity, the product and ligand B were separated after the alcohol was transformed into its 2,4,6-trimethylbenzenesulfonate. For the details, see the Supporting Information.
57. This recovered ligand was shown to be as effective (asymmetric induction, yield, and reproducibility) as the original ligand.