Process for producing optically active 2-norbornanone

Details Process for producing optically active 2-norbornanone Process for producing optically active 2-norbornanone

1994-08-19

1996-03-12

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

549449, 562502, C07C 4541

Patent

active

054987997

ABSTRACT:
An optically active 5-methylenedioxolan-4-one derivative is subjected to Diels-Alder reaction with cyclopentadiene, and the resulting Diels-Alder reaction product is hydrolyzed to convert it into an optically active 2-hydroxynorbornene-2-carboxylic acid, which is then subjected to catalytic hydrogenation to form an optically active 2-hydroxynorbornane-2-carboxylic acid. The hydroxycarboxylic acid is subjected to oxidative decarboxylation to obtain an optically active 2-norbornanone.

REFERENCES:
patent: 4007211 (1977-02-01), Trost et al.
patent: 4812476 (1989-03-01), Imwinkelried et al.
patent: 5214197 (1993-05-01), Hayashi et al.
patent: 5266728 (1993-11-01), Yoshida et al.
Chemische Berichte, vol. 122, No. 2, Feb. 1989, Jochen Mattay, et al., "Asymmetric Induction in the Diels-Alder Reaction of Chiral (2S)-2-(tert-Butyl)5-Methylene-1,3-Dioxolan-4-One')", pp. 327-330.
Tetrahedron, vol. 49, No. 36, pp. 7871-7882, 1993, A. L. J. Beckwith, et al., "Some Diastereoselective Radical Reactions of Substituted 1.3-Dioxolan-4-Ones".
Fieser et al, "Reagents for Organic Synthesis", p. 1308 (1967).

Affiliated with

Also associated with

Rating

Process for producing optically active 2-norbornanone does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing optically active 2-norbornanone, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing optically active 2-norbornanone will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2101656