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Tetrahedron: Asymmetry

Volumn 6, Issue 3, 1995, Pages 637-638

Catalytic chirally self-replicating molecule. Asymmetric autocatalytic reaction of a zinc alkoxide of chiral 1-ferrocenyl-2-methylpropan-1-ol

(3) Soai, Kenso a Hayase, Tadakatsu a Takai, Kazuhisa a

a TOKYO UNIVERSITY OF SCIENCE (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0028899406 PISSN: 09574166 EISSN: 1362511X Source Type: Journal
DOI: 10.1016/0957-4166(95)00047-S Document Type: Article

Times cited : (58)

References (22)

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- Reviews:
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3
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4
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- Asymmetric self-catalytic reaction. Self-production of chiral 1-(3-pyridyl)alkanols as chiral self-catalysts in the enantioselective addition of dialkylzinc reagents to pyridine-3-carbaldehyde
- (1990) Journal of the Chemical Society, Chemical Communications , pp. 982
- Soai¹ Niwa² Hori³

5
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- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 789
- Soai¹ Hayase² Shimada³ Isobe⁴

6
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- For the asymmetric autoinduction (not self-replication), see
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 7265
- Alberts¹ Wynberg²

7
- 33751499922
- (1991) J. Org. Chem. , vol.56 , pp. 6740
- Danda¹ Nishikawa² Otaka³

8
- 37049084187
- Asymmetric synthesis. Part 19. Asymmetric autocatalysis of (R)-1-phenylpropan-1-ol mediated by a catalytic amount of amine in the addition of diethylzinc to benzaldehyde
- For the achiral amine mediated asymmetric autoinduction
- (1993) Journal of the Chemical Society, Perkin Transactions 1 , pp. 885
- ShengJian¹ Yaozhong² Aiqiao³ Guishu⁴

9
- 0026634324
- Although the induction of 14.3% e.e. is reported using 1-phenylpropanol in the ethylation of benzaldehyde, a contradictory result has been reported in ref. 4a. For the replication of a molecule which does not produce new chiralities, see
- (1992) Nature , vol.358 , pp. 203
- Orgel¹

10
- 0001711390
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 8877
- Winner¹ Conn² Rebek³

11
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- K. Soai, T. Hayase, K. Takai and T. Sugiyama, J. Org. Chem., in press. The configuration is tentatively assigned based on the results that (1S, 2R)-N,N-dialkylnorephedrines catalyze the addition of dialkylzincs from the Si face of the aldehydes

12
- 33751499839
- (1991) J. Org. Chem. , vol.56 , pp. 4264
- Soai¹ Yokoyama² Hayasaka³

13
- 26444467796
- The direction of the optical rotation [(S)-(+)] was in good agreement with that [(R)-(−), tentatively assigned] described in ref. 5g. For the preparation of chiral ferrocenyl alcohols, see
- (1972) J. Chem. Educ. , vol.49 , pp. 294
- Gokel¹ Ugi²

14
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- (1989) Tetrahedron Lett. , vol.30 , pp. 2061
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15
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- (1989) Tetrahedron Lett. , vol.30 , pp. 5313
- Yamazaki¹ Hosono²

16
- 0002904790
- (1990) J. Organomet. Chem. , vol.382 , pp. 19
- Noyori¹ Suga² Kawai³ Okada⁴ Kitamura⁵ Oguni⁶ Hayashi⁷ Kaneko⁸ Matsuda⁹

17
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- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1763
- Matsumoto¹ Ohno² Lu³ Hayashi⁴ Oguni⁵ Hayashi⁶

18
- 0001599919
- (1994) J. Organomet. Chem. , vol.476 , pp. 215
- Wright¹ Frambes² Reeves³

19
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- (1963) Die Makromolekulare Chemie , vol.64 , pp. 190
- Ishimori¹ Tsuruta²

20
- 84914088278
- 4), evaporated under reduced pressure. The purification of the residue by silica gel TLC (eluent, hexane/EtOAc = 5/1) afforded a mixture of catalyst 2 (0.0517g) and the newly formed 2 in a total amount of 0.2462g. Thus the amount of the newly formed 2 was 0.1945g (0.75 mmol, 75%) (0.2462 − 0.0517 = 0.1945). HPLC [[Truncated]]

21
- 84914088277
- 2Zn without using chiral 3 afforded racemic2 in 69% yield as the result of the formation of racemic autocatalyst 3.

22
- 84914088276
- Financial support by The SUT Special Grant for Research Promotion 1994–1995 is gratefully acknowledged.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.