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CAS indexed 86 chemical substances from this document.
CAS subject entries for this document include: Bronsted acids; Carboxylic acids, reactions; Sulfonic acids, reactions; and 18 additional concepts. | |
CAPLUS COPYRIGHT 2003 ACS on STN
| TITLE:
| Enantioselective transformation of .alpha.,.beta.-unsaturated ketones using chiral organic catalysts |
| INVENTOR(S):
| MacMillan, David W. C.; Northrup, Alan B. |
| PATENT ASSIGNEE(S):
| California Institute of Technology, USA |
| SOURCE:
| PCT Int. Appl., 46 pp. CODEN: PIXXD2 |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- --------------- --------
WO 2003047740 A2 20030612 WO 2002-US39065 20021205
WO 2003047740 A3 20030904
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN,
CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH,
GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR,
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH,
PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ,
UA, UG, US, UZ, VN, YU, ZA, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU,
TJ, TM
RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AT, BE, BG,
CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL,
PT, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML,
MR, NE, SN, TD, TG
ABSTRACT:
Nonmetallic org. catalysts are provided that facilitate the enantioselective reaction of .alpha.,.beta.-unsatd. ketones. The catalysts are chiral imidazolidinone compds. I or II there acid addn. salts [R1 = C1-6-alkyl; R2 = Ph, 2-methylfuryl; R3, R4 = H; R5 = (un)substituted Ph (with 1 or 2 substituents selected from halo, OH, C1-6-alkyl)]. The chiral imidazolinones are useful in catalyzing a wide variety of reactions, including cycloaddn. reactions, Friedel-Crafts alkylation reactions, and Michael addns. Thus, I [R1 = Me, R2 = 5-methyl-2-furyl, R3 = R4 = H, R5 = Ph] was used to catalyze the Diels-Alder reaction of cyclopentadiene with MeCH:CHCOEt to give 89% (+)-2-endo-3-exo-[3-methylbicyclo[2.2.1]hept-5-en-2-yl]propan-1-one (90% e.e.).
Updated 5/9/2007 12:53:07 PM
