Kinetic resolution and isomerization of 2,5-disubstituted pyrrolines

Chirality

Volumn 12, Issue 5-6, 2000, Pages 476-478

  Yun, Jaesook ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cyclic imines; Enantiomeric excess; Hydrosilylation; Titanocene catalyst

Indexed keywords

IMINE; PYRROLINE DERIVATIVE; TITANOCENE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ISOMERISM; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0034119269     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<476::aid-chir31>3.0.co;2-b     Document Type: Article

References (9)

1. Verdaguer X, Lange UEW, Reding MT, Buchwald SL. Highly enantioselective imine hydrosilylation using (S,S)-ethylenebis(η5-tetrahydroindenyl)titanium difluoride. J Am Chem Soc 1996;118:6784-6785.
2. Verdaguer X, Lange UEW, Buchwald SL. Amine additives greatly expand the scope of asymmetric hydrosilylation of imines. Angew Chem Int Ed 1998;37:1103-1107.
3. (a) Willoughby CA, Buchwald SL. Asymmetric titanocene-catalyzed hydrogenation of imines. J Am Chem Soc 1992;114:7562-7564.
4. (b) Willoughby CA, Buchwald SL. Synthesis of highly enantiomerically enriched cyclic amines by the catalytic asymmetric hydrogenation of cyclic imines. J Org Chem 1993;58:7627-7629.
5. For a review of asymmetric hydrogenation of imines, see: Blaser H-U, Spindler F. Hydrogenation of imino groups. In: Jacobsen EN, Pfaltz A, Yamamoto H, editors. Comprehensive asymmetric catalysis. Berlin: Springer; 1999. p 247-265. For a review of asymmetric hydrosilylation of imines, see: Nishiyama H. Hydrosilylation of carbonyl and imino groups. In: ibid, p 267-287.
6. For a review of asymmetric hydrogenation of imines, see: Blaser H-U, Spindler F. Hydrogenation of imino groups. In: Jacobsen EN, Pfaltz A, Yamamoto H, editors. Comprehensive asymmetric catalysis. Berlin: Springer; 1999. p 247-265. For a review of asymmetric hydrosilylation of imines, see: Nishiyama H. Hydrosilylation of carbonyl and imino groups. In: ibid, p 267-287.
7. For a general reference on kinetic resolution, see: Kagan HB, Fiaud JC. Kinetic resolution. In: Eliel EL, Wilen SH, editors. Topics in stereochemistry. New York: John Wiley & Sons; 1988. p 249-331.
8. Viso A, Lee NE, Buchwald SL Kinetic resolution of racemic disubstituted 1-pyrrolines via asymmetric reduction with a chiral titanocene catalyst. J Am Chem Soc 1994;116:9373-9374.
9. Masamune S, Choy W, Peterson JS, Sita LR. Double asymmetric synthesis and a new strategy for stereochemical control in organic synthesis. Angew Chem Int Ed Engl 1985;24:1-30.