90130-90-8

Upstream product

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 31929-07-4 2-allyl-2-methyl-1,3-cyclohexanedione 
• 193096-69-4 (6R,7R)-6-Allyl-6-methyl-1,4-dioxa-spiro[4.5]decan-7-ol 

Downstream Products

• 316805-96-6 (2S,3S)-3-[(tert-Butyldimethylsilyl)oxy]-2-methyl-2-(2-oxopropyl)cyclohexan-1-one 
• 316805-95-5 (2S,3S)-3-[(tert-Butyldimethylsilyl)oxy]-2-methyl-2-(2-propenyl)cyclohexan-1-one 
• 90105-51-4 (2S,3S)-3-hydroxy-2-methyl-2-(prop-2-enyl)cyclohexan-1-one 
• 90130-91-9 (2R,3S)-3-Hydroxy-2-methyl-2-(2-propenyl)cyclohexan-1-one 

Relevant academic research and scientific papers

Desymmetric enantioselective reduction of cyclic 1,3-diketones catalyzed by a recyclable p-chiral phosphinamide organocatalyst

The P-stereogenic phosphinamides are a structurally novel skeletal class which has not been investigated as chiral organocatalysts. However, chiral cyclic 3-hydroxy ketones are widely used as building blocks in the synthesis of natural products and bioactive compounds. However, general and practical methods for the synthesis of such chiral compounds remain underdeveloped. Herein, we demonstrate that the P-stereogenic phosphinamides are powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol displays a broad substrate scope that is amenable to a series of cyclic 2,2-disubstituted five- and six-membered 1,3-diketones. The chiral cyclic 3-hydroxy ketone products bearing an all-carbon chiral quaternary center could be obtained with high enantioselectivities (up to 98% ee) and diastereoselectivities (up to 99:1 dr). Most importantly, the reactions could be practically performed on the gram scale and the catalysts could be reused without compromising the catalytic efficiency. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species. The results disclosed herein bode well for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.

Comparative reductive desymmetrization of 2,2-disubstituted-cycloalkane-1,3-diones

Reductive desymmetrization of 2-methyl-2-substituted-cycloalkane-1,3-diones can be effected using either NaBH4 in DME or lithium tri-tert-butoxyaluminum hydride (LTBA) in THF at -60 °C. The former is a new approach that offers slightly greater

First stereoselective synthesis of the versatile chiral building block (7aR)-5,6-dihydro-7a-methyl-1H-indene-2,7(4H,7aH)-dione

A versatile chiral building block (7aR)-5,6-dihydro-7a-methyl-1H-indene-2,7(4H,7aH)-dione (4) was firstly enantiomerically synthesized from the microbial transformation ketol product 6 in 61.3% overall yield and over 96% ee.

Asymmetric hydrolysis of pro-chiral 3,3-disubstituted 2,4-diacetoxy-cyclohexa-1,4-dienes

Asymmetric enzymatic hydrolysis of pro-chiral 3,3-disubstituted 2,4-diacetoxycyclohexa-1,4-dienes 2 affords in high yields optically pure 2,2-disubstituted 3-acetoxycyclohex-3-enones 1 (>98% ee). Under mild conditions Candida cylindracea lipase (enzyme/substrate ratio = 2%) hydrolyses specifically the pro-S enol ester function of the pro-chiral starting material 2.

Asymmetric Microbial Reduction of Prochiral 2,2-Disubstituted Cycloalkanediones

Asymmetric microbial reduction of a series of 2,2-disubstituted 1,3-cycloalkanediones with bakers' yeast was examined as an example of an enzyme-catalyzed distinction of a substrate containing two trigonal carbonyl centers with stereoheterotropic faces an

CHIRAL CYCLOHEXANOID SYNTHETIC PRECURSORS VIA ASYMMETRIC MICROBIAL REDUCTION OF PROCHIRAL CYCLOHEXANEDIONES

Microbial reduction of various 2,2-disubstituted-1,3-cyclohexanediones with bakers' yeast provides efficient access to chiral cyclohexanoid synthetic precursors.