147168-89-6

Upstream product

• 137329-22-7 (+)-1-isocyanato-7,7-dimethylbicyclo[2.2.1]heptan-2-one 
• 38989-02-5 (1S,4R)-1-amino-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one 
• 21286-54-4 Camphorsulfonyl chloride 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 464-78-8 (1S)-(+)-ketopinic acid 

Downstream Products

• 292039-09-9 (1S,5R,7R)-10,10-dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.0^1,5]dec-2-ene 
• 147168-92-1 N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 
• 147253-91-6 N-<(2R,3R)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 
• 292039-13-5 (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]dec-2-ene 
• 184680-35-1 (1S,5R,7R)-3,3,10,10-Tetramethyl-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]decane 

Relevant academic research and scientific papers

Asymmetric aldol reactions: A novel model for switching between chelation- and non-chelation-controlled aldol reactions

A new camphor-based N-propionyloxazolidinethione provides remarkable levels of asymmetric induction for both chelation- and non-chelation-controlled aldol processes. While the aldol condensation of the derived di-n-butylboryl enolate with various aldehyde

"Non-Evans" syn aldol via aldolization of chlorotitanium enolate with TiCl4/ aldehyde complex

Direct aldolizations of chlorotitanium enolate derived from camphor-based oxazolidinethione with 1:1 TiCl4-aldehyde complex give "non-Evaner" syn aldol with excellent diastereoselectivity.

Enantioselective addition of dialkylzinc to aromatic aldimines mediated by camphor-derived chiral β-amino alcohols

The enantioselective addition of diethylzinc or dimethylzinc to N-(diphenylphosphinoyl)imines mediated by 1 or 2 could be achieved in high yields (70-97%) and enantioselectivities (85-98% ee). The catalytic loading of 1 or 2a could be reduced to 10 mol% f

METHOD OF ENANTIOSELECTIVE ADDITION TO IMINES

The present invention relates to a method of enantioselective addition to imines, including: reacting R2CH═NY with R3ZnR4 in the presence of a compound represented by the following formula (I), in which Y, R1, R

A new chiral oxazoline derived from camphor and its conversion to (R)-2-methylalkanoic acids

(1S,5R,7R)-(-)-10,10-Dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.01,5]dec-2-ene 2 was prepared in 95% yield from (1S)-1-amino-2-exo-hydroxyapocamphane 1. The chiral oxazoline could be alkylated (LDA/THF/-78°C/RX, RX=ethyl, n-propyl, n-butyl iodides or benzyl bromide) to 3 in 95% yield and >95% diastereoselectivity, and the products hydrolysed to (R)-2-methylalkanoic acids 4 (43-47% yield, 93-98% e.e.). Copyright (C) 2000 Elsevier Science Ltd.

Synthesis of several novel optically active nitroxyl radicals

Optically active nitroxyl radicals are prepared from enantiomerically pure bicyclic tempenoids. (-)-Camphoxyl radical (-)-4 derived from commercially available oxazolidinone (-)-1 and (+)-camphoxyl radical (+)-4 derived from (-)-camphene are readily prepared, conformationally rigid, enantiomeric nitroxyl radicals. (-)-Camphorsulphonic acid is used to prepare two additional optically active nitroxyl radicals 9 and 12.