Cycloalkyl-based chiral auxiliaries and method making the same

Details Cycloalkyl-based chiral auxiliaries and method making the same Cycloalkyl-based chiral auxiliaries and method making the same

1992-03-20

1993-11-16

Cintins, Marianne M.

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

Organic compounds

Oxygen containing

568810, 568821, 568828, 568834, 568838, 435280, C07C 29159

Patent

active

052625710

ABSTRACT:
A process of synthesizing enantiomerically pure compounds defined by Formula V, ##STR1## which are useful as chiral auxiliaries is disclosed. The process comprises, first, combining a base of Formula Y.sup.- Z.sup.+ (Formula I), wherein Y.sup.- is an organic anion and Z.sup.+ is an inorganic cation, with a compound of Formula II, ##STR2## wherein R.sub.1 is a C.sub.1 -C.sub.4 alkyl group and R.sub.2 is the same as R.sub.1, or wherein R.sub.1 and R.sub.2 together form cyclopentane or cyclohexane, and wherein R.sub.3 is a substituted or unsubstituted aryl group, to form a compound defined by Formula III, ##STR3## then: (b) reacting the compound of Formula III with a cyclic epoxide defined by Formula IV, ##STR4## wherein n is 1, 2, or 3, to form a racemic mixture of a compound defined by Formula V. ##STR5## In a preferred embodiment, the method further comprises stereospecifically esterifying one of the enantiomers of the racemic mixture of compound (V) and a carboxylic acid with an enzyme in an organic solvent, wherein said acid is a C.sub.2 -C.sub.20 alkyl acid, benzoic acid or a C.sub.2 -C.sub.14 alkyl benzoic acid, and then separating the esterified enantiomer from the non-esterified enantiomer.

REFERENCES:
patent: 3109018 (1963-10-01), Hanover
patent: 3607651 (1971-09-01), Moroz
patent: 3943181 (1976-03-01), Fleischer et al.
patent: 4418225 (1983-11-01), House
patent: 4720558 (1988-01-01), Kaulen
patent: 4916074 (1990-04-01), Yoshida et al.
patent: 4962031 (1990-10-01), Yoshida et al.
patent: 4963492 (1990-10-01), Keller et al.
patent: 4996158 (1991-02-01), Oda et al.
patent: 5021345 (1991-06-01), Urban et al.
patent: 5032523 (1991-07-01), Amano et al.
patent: 5057427 (1991-10-01), Wald et al.
Carey & Sundberg; Adv. Org. Chem., 2nd ed., Part B: Rxns & Syn; 1984, pp. 498-506.
Okumura et al; Biochimica et Biophysica Acta, 575 (1979); pp. 156-165.
R. Lawrence, "The Resolution and Use of Chiral Auxiliaries in Asymmetric Synthesis," Dissertation presented to the faculty of the University of Texas at Austin (UMI, Ann Arbor, Mich.) Dec. 1988.
R. Benkeser et al., J. Am. Chem. Soc. 85, 3984-3989 (1963).
G. Langrand et al., Tetrahedron Letters, 26, No. 15, 1857-1860 (1985).
W. Oppolzer et al., Helvetica Chimica Acta 63, Fasc. 7, 2015-2018 (1980).
J. Whitesell, Acc. Chem. Res. 18, 280-284 (1985).
J. Whitesell and R. Lawrence, CHIMIA 40, No. 9, 318-322 (1986).
D. Wilhelm et al., J. Am. Chem. Soc. 106, No. 2, 361-367 (1984).

Affiliated with

Also associated with

Rating

Cycloalkyl-based chiral auxiliaries and method making the same does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Cycloalkyl-based chiral auxiliaries and method making the same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cycloalkyl-based chiral auxiliaries and method making the same will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-23723