93714-16-0

Upstream product

• 127184-17-2 C₂₃H₃₉BO 
• 123-72-8 butyraldehyde 
• 67-64-1 acetone 
• 25290-14-6 4-Hydroxy-heptan-2-on 
• 1243288-99-4 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)heptan-2-one 
• 157954-40-0 1,1-Bis(phenylthio)-2-methyl-1-hepten-4-ol 

Relevant academic research and scientific papers

Metal-free catalytic boration at the β-position of α,β-unsaturated compounds: A challenging asymmetric induction

Enantiomerlcally enriched secondary organoboronates containing β-carbonyl functional groups have been prepared using an unprecedented organocatalytic system (see scheme). The use of chiral tertiary phosphorus compounds induced ee values of up to 95 % in the absence of transition metals. (Figure Presented).

Preparation of the Enantiomerically Enriched Isomers of the Odorous Cyclic Ethers Clarycet, Florol, and Rhubafuran by Enzymatic Catalysis

All the enantiomerically enriched stereoisomers of Clarycet (1), Florol (2), and Rhubafuran (3) were prepared by biocatalysis routes. Their absolute configurations were established, and their olfactory properties were fully evaluated.

Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts

(Equation presented) The enantioselective aldol reaction using a novel binuclear zinc catalyst of acetone with several aldehydes gave products in good yields (62-89%) with a high level of enantioselectivity (ee = 76-92%).

Resolution of homoallylic alcohols containing dithioketene acetal functionalities. Synthesis of optically active γ-lactones by a combination of chemical and enzymatic methods

Racemic homoallylic alcohols 1-3 containing dithioketeneacetal functionalities were prepared by addition of aldehydes to the allylic anions of ketene dithioacetals or 2-alkenyl-1,3-dithiane in a regio- and stereoselective manner. Lipase-catalyzed hydrolyses of the corresponding acetates 7-9 afforded optically active alcohols 1-3, which were treated with mercuric chloride to give γ-lactones such as natural hop lactone, whiskey lactone, and cognac lactone.

ENANTIO- AND DIASTEREOSELECTIVE ALDOL REACTIONS OF ACHIRAL ETHYL AND METHYL KETONES WITH ALDEHYDES: THE USE OF ENOL DIISOPINOCAMPHEYLBORINATES.

Enol diisopinocampheylborinates, derived from achiral ethyl and methyl ketones by enolisation in the presence of tertiary amine bases (iPr2NEt or Et2N), undergo enantio- and diastereoselective aldol reactions with aldehydes.The reagents employed, (+)- and (-)-(Ipc)2BOTf, are easily prepared in enantiomerically pure form in two steps from (-)- and (+)-α-pinene, respectively.The aldol reaction between ethyl ketones and aldehydes using (+)- or (-)-(Ipc)2BOTf/iPr2NEt in dichloromethane gives, via the derived chiral Z-enol borinates, syn-α-methyl-β-hydroxy ketones in good enantiomeric excess (66-93percent ee) and with high diastereoselectivity (>95percent).In contrast, the anti-selective aldol reaction of diethylketone via the isomeric E-enol diisopinocampheylborinate (by enolisation with (-)-(Ipc)2BCl) with methacrolein proceeds with negligible enantioselectivity.Use of both the triflate and chloride reagents in the aldol reaction of methyl ketones with aldehydes gives β-hydroxy ketones in moderate enantiomeric excess (53-78percent ee) with a reversal in the enantioface selectivity of the aldehyde compared to the corresponding ethyl ketone syn aldol.This variable selectivity is interpreted as evidence for the participation of competing chair and boat transition states.Other chiral dialkylboron triflate reagents investigated led to reduced enantioselectivities in diethylketone-aldehyde aldol reactions.

ALDOL REACTIONS OF METHYLKETONES USING CHIRAL BORON REAGENTS: A REVERSAL IN ALDEHYDE ENANTIOFACE SELECTIVITY

The enantioselectivity of aldol additions of methylketones to aldehydes using(-)-(Ipc)2BOTf, (-)-1, and Pri2NEt is generally lower(53-78percent ee) than that for the corresponding ethylketone reaction and occurs with the opposite sense of aldeh