(2 S ) - (-) - exo - (dimethylamino) isoborneol

Structural formula
General
Surname	(2 S ) - (-) - exo - (dimethylamino) isoborneol
other names	3- (Dimethylamino) -1,7,7-trimethyl- [1 R - ( exo , exo )] - bicyclo [2.2.1] heptan-2-ol ( IUPAC ) ; DAIB;
Molecular formula	C 12 H 23 NO
Brief description	colorless oil
External identifiers / databases
PubChem	3368226
ChemSpider	2613905
Wikidata	Q150508
properties
Molar mass	198.18 g mol −1
Physical state	firmly
boiling point	150 ° C
solubility	good in ethanol , toluene and dichloromethane
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

(2 S ) - (-) - exo - (dimethylamino) isoborneol , mostly abbreviated as DAIB , is an organic chemical compound that can be structurally derived from isoborneol . The chiral compound is sometimes used as an enantioselective catalyst .

Extraction and presentation

The starting product for the synthesis of (2 S ) - (-) - exo - (dimethylamino) isoborneol is (1 R , 4 S ) - (-) - camphorquinone monoxime. From this, (2 S ) - (-) - 3- exo- aminoisoborneol is produced by reduction with lithium aluminum hydride . To introduce the still missing methyl groups, a carbamate is first produced with triphosgene and then the first methyl group is introduced with methyl iodide . In order to obtain the final product, the carbamate is finally reduced with lithium aluminum hydride.

Properties and use

DAIB is a colorless liquid that dissolves well in most organic solvents such as ethanol , toluene and dichloromethane . The compound acts as an enantioselective catalyst in the reduction of aldehydes with organic zinc compounds . The reaction of benzaldehyde with diethylzinc under DAIB catalysis produces ( S ) -1-phenyl-1-propanol with an enantiomeric excess of 95.4% ee and 97% yield. The compound thus enables a high enantiomeric excess in the product, although the catalyst has a significantly lower enantiomeric purity.

DAIB decomposes slowly in air and must therefore be stored under inert gases such as nitrogen or argon .

Individual evidence

↑ ^a ^b ^c ^d James D. White, Duncan J. Wardrop, and Kurt F. Sundermann: (2S) - (-) - exo- (dimethylamino) isoborneol [(2S) - (-) - DAIB] Template: Linktext-Check / Escaped In: Organic Syntheses . 79, 2002, p. 130, doi : 10.15227 / orgsyn.079.0130 ( PDF ).
↑ ^a ^b Grant R. Krow, Kevin C. Cannon: Encyclopedia of Reagents for Organic Synthesis: (1R, 2S, 3R, 4S) -3-Dimethylamino-1,7,7-trimethylbicyclo [2.2.1] heptane-2- oil. October 15, 2003.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Masato Kitamura, Hiromasa Oka, Seiji Suga, Ryoji Noyori : Catalytic enantioselective addidion of dialkylzincs to aldehydes using (2S) - (-) - exo- (dimethylamino) isoborneol [(2S) -DAIB]: (S) -1-phenyl -1-propanol Template: Linktext-Check / Escaped In: Organic Syntheses . 79, 2002, p. 139, doi : 10.15227 / orgsyn.079.0139 ( PDF ).

[OrgSynth-1] James D. White, Duncan J. Wardrop, and Kurt F. Sundermann: (2S) - (-) - exo- (dimethylamino) isoborneol [(2S) - (-) - DAIB] Template: Linktext-Check / Escaped In: Organic Syntheses . 79, 2002, p. 130, doi : 10.15227 / orgsyn.079.0130 ( PDF ).

[grant-2] Grant R. Krow, Kevin C. Cannon: Encyclopedia of Reagents for Organic Synthesis: (1R, 2S, 3R, 4S) -3-Dimethylamino-1,7,7-trimethylbicyclo [2.2.1] heptane-2- oil. October 15, 2003.

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Masato Kitamura, Hiromasa Oka, Seiji Suga, Ryoji Noyori : Catalytic enantioselective addidion of dialkylzincs to aldehydes using (2S) - (-) - exo- (dimethylamino) isoborneol [(2S) -DAIB]: (S) -1-phenyl -1-propanol Template: Linktext-Check / Escaped In: Organic Syntheses . 79, 2002, p. 139, doi : 10.15227 / orgsyn.079.0139 ( PDF ).