184840-87-7

Upstream product

• 110-44-1 sorbic Acid 
• 81838-85-9 tert-butyl (2E,4E)-2,4-hexadienoate 
• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 184840-85-5 tert-Butyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 

Downstream Products

• 1606140-22-0 (2S,3S)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-2-ol 
• 1606140-20-8 (2R,3S)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-2-ol 
• 1606140-24-2 (2S,3S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran 
• 127001-34-7 N-Benzylidene<(R)-(-)-α-methylbenzyl>amine N-oxide 
• 184840-89-9 (E)-6-hydroxyhex-3-en-2-one 
• 184840-88-8 (5R,αR)-(E)-5-[N-Benzyl-N-(α-methylbenzyl)aminooxy]hex-3-en-1-ol 

Relevant academic research and scientific papers

Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside, methyl N-Boc-2-deoxy-2-amino-d-threoside and methyl N-Boc-2,3-dideoxy-3-amino-l- arabinopyranoside

The asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside and methyl N-Boc-2-deoxy-2-amino-d-threoside have been achieved from sorbic acid, in six and eight steps, and in 35 and 13% overall yield, respectively. Diastereoselective aminohydroxy

Asymmetric synthesis of (R)-hexane-1,5-diol, (R)-hex-3-ene-1,5-diol and (R)-6-methylhept-5-en-2-ol (sulcatol) employing a tandem asymmetric conjugate addition and stereospecific Meisenheimer rearrangement protocol

Highly stereoselective conjugate addition of lithium (R)-N-methyl-(α-methylbenzyl)amide to tert-butyl (E,E)-hexa-2,4-dienoate, followed by reduction of the ester to the corresponding alcohol, affords a substrate which undergoes, upon oxidation, a stereospecific Meisenheimer rearrangement to give a single diastereomer of the corresponding trialkylhydroxylamine. The analogous N-benzyl adduct gives lower yields in the oxidation-rearrangement reaction. If the ester is not reduced to the alcohol, N-oxidation leads to Cope elimination, not Meisenheimer rearrangement. Cleavage of the N-O bond gives (R)-hex-3-ene-1,5-diol, and hydrogenation of the double bond affords (R)-hexane-1,5-diol in high ee. This methodology has been applied to the synthesis of the insect pheromone (R)-6-methylhept-5-en-2-ol (sulcatol) from tert-butyl (E,E)-hexa-2,4-dienoate, via a sequence involving conjugate addition of the lithium amide, Grignard addition to the ester, Meisenheimer rearrangement, hydrogenation of the double bond, dehydration of the tertiary alcohol and finally N-O bond cleavage.