1992
DOI: 10.1055/s-1992-21419
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Enantioselective Addition of Diethylzinc to Aldehydes in the Presence of Chiral Titanium Reagent Modified withN-Sulfonylated Amino Alcohol

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Cited by 42 publications
(14 citation statements)
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“…12 Since then, extensive synthetic studies were conducted and a-hydroxy sulfonamides and bissulfonamides were proven to be very efficient ligands for additions of dialkylzincs. [13][14][15][16][17] Although the exact mechanism of the process is not known, recent structural and mechanistic investigations showed that the active catalytic intermediates could be an ethyltitanium species derived from the transfer of an ethyl group from zinc to titanium or a bimetallic species containing an ethylzinc compound. 15 Both ligand accelerated diethylzinc additions and alkyltitanium additions to carbonyl compounds exhibit excellent chemoselectivity.…”
Section: Introductionmentioning
confidence: 99%
“…12 Since then, extensive synthetic studies were conducted and a-hydroxy sulfonamides and bissulfonamides were proven to be very efficient ligands for additions of dialkylzincs. [13][14][15][16][17] Although the exact mechanism of the process is not known, recent structural and mechanistic investigations showed that the active catalytic intermediates could be an ethyltitanium species derived from the transfer of an ethyl group from zinc to titanium or a bimetallic species containing an ethylzinc compound. 15 Both ligand accelerated diethylzinc additions and alkyltitanium additions to carbonyl compounds exhibit excellent chemoselectivity.…”
Section: Introductionmentioning
confidence: 99%
“…In all cases the major enantiomer of the produced 1-phenyl-propanol possessed the S configuration. The highest enantioselectivities were obtained with chiral ligand 5c (Table 1, entries [8][9][10][11][12]. By increasing the ratio of ligand 5c to benzaldehyde, an increase in the enantioselectivity of (S)-1-phenyl-1-propanol was observed, and the best enantioselectivity (78% ee) was obtained, when 20 mol% of 5c was used (Table 1, entry 12).…”
Section: Resultsmentioning
confidence: 99%
“…After optimizing the best conditions for the reaction of diethylzinc with benzaldehyde, we applied the same condition to other aromatic aldehydes. According to the obtained results by 5c (Table 1, entries [8][9][10][11][12] and similarity of the ees in +10 °C and -10 °C the optimized reactions were carried out at +10 °C and -30 °C. The results for the addition of diethylzinc in the presence of 5c are summarized in Table 2.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…1 For example, amino alcohols, [2][3][4][5] hydroxypyridine, 6 diol, 7 hydroxy carboxylic acids, 8 α-amino amide, 9 α-hydroxy amides 10 were employed in this asymmetric addition to aldehydes widely. Recently, a series of imino alcohols 11 and hydroxysulfonamides [12][13][14][15] were employed to catalyze this addition reaction and to control the stereoselectivity of this reaction. Moreover, by the optimization of ligands, the enantioselective addition of ketone with dialkylzinc was realized.…”
Section: Introductionmentioning
confidence: 99%