2013
DOI: 10.1002/chem.201300478
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Highly Enantioselective Aldol Reactions between Acetaldehyde and Activated Acyclic Ketones Catalyzed by Chiral Primary Amines

Abstract: Highly enantioselective cross-aldol reactions between acetaldehyde and activated acyclic ketones are reported for the first time. Various acyclic ketones, such as saturated and unsaturated keto esters, reacted with acetaldehyde in the presence of a chiral primary amine and a Brønsted acid to afford optically enriched tertiary alcohols in good yields and with excellent enantioselectivities. Trifluoromethyl ketones were tolerable under the reaction conditions, thereby affording the trifluoromethyl carbinol in go… Show more

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Cited by 31 publications
(14 citation statements)
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“…As recorded in Table 3, the primary amine 1d exhibited generally high to excellent enantioselectivities ranging from 83% to 93% ee and good yields for most of a,b-unsaturated ketones tested (entries [1][2][3][4][5][6][7][8][9][10][11], with the exception of the case involving heteroaromatic substrates, in which moderate yields were obtained (entries 12 and 13). Extending these reaction conditions to other trifluoroacetophenones was highly successful, giving rise to trifluoromethylated b-hydroxycarbonyl compounds with 86-99% ee (entries 14-17).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…As recorded in Table 3, the primary amine 1d exhibited generally high to excellent enantioselectivities ranging from 83% to 93% ee and good yields for most of a,b-unsaturated ketones tested (entries [1][2][3][4][5][6][7][8][9][10][11], with the exception of the case involving heteroaromatic substrates, in which moderate yields were obtained (entries 12 and 13). Extending these reaction conditions to other trifluoroacetophenones was highly successful, giving rise to trifluoromethylated b-hydroxycarbonyl compounds with 86-99% ee (entries 14-17).…”
Section: Resultsmentioning
confidence: 99%
“…10 Very recently, these chiral amines were successfully applied in cross aldol reactions of acetaldehyde with unsaturated keto-esters, yielding enantiomerically enriched tertiary alcohols with excellent enantioselectivity. 11 In our continuous efforts toward exploring primary amine catalyzed aldol reactions with ketones and synthesizing trifluoromethylated organic compounds, we herein report a cross aldol of a,b-unsaturated ketones with trifluoroacetophenone to allow the synthesis of trifluoromethylated b-hydroxycarbonyl compounds bearing a quaternary carbon stereogenic center.…”
Section: Introductionmentioning
confidence: 99%
“…The au-thors reported also the asymmetric aldol reaction of an aromatic CF 3 ketone and of aC F 3 -tethered a,b-unsaturated ketonew ith acetaldehyde,w hich gave the corresponding aldol products in high yields and enantioselectivities( Scheme6). [12] The first applicationo ft his smalle nolizable aldehyde in the direct cross-aldol reaction with a-ketophosphonates was reportedb yZ hao and co-workers to afford a-hydroxyphosphonate derivatives, knowna sh ighly biologically active compounds. The screening of catalysts and additives showedt hat the 9-amino-9-deoxy-epi-quinine catalyst 7 in combination with 4-methoxybenzoic acid (MBA) as an additive provided the aldol products in moderate to high yields and excellent enantioselectivities (Scheme 7).…”
Section: Cross-aldol Reactionsmentioning
confidence: 99%
“…该手性伯胺可以有效催化丙酮与芳香醛、酮酸酯以 及不饱和酮酸酯的不对称 Aldol 反应 [12] (Scheme 2). 最 近, 我们首次发现, 该手性伯胺催化剂能有效催化乙醛 与活泼非环状酮化合物, 如不饱和酮酸酯、三氟甲基酮 等的高对映选择性 Aldol 反应 [13] (Scheme 3) .…”
Section: δ-戊内酯 尤其是 4-羟基-δ-戊内酯在有机合成中具 有重要的作用 δ-戊内酯结构广泛存在于许多天然产物 和非天然产物中unclassified
“…c Determined by chiral HPLC. [12] . c Determined by chiral HPLC and the ee in parentheses is for the crystallization from hexane/ethyl acetate.…”
Section: -羟基-3-三氟甲基-4-戊烯酸(7)的碘内酯化反应mentioning
confidence: 99%