Journal article

ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3]

Abstract:: Syntheses of both title compounds have been achieved with excellent stereocontrol using chiral acetate enolate equivalents derived from the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COCH3]. The different diastereoselectivities in the two syntheses are rationalised in terms of the concept of double asymmetric induction and the transition state models for the aldol reactions of such enolates are discussed. © 1993.

Publication status:: Published

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APA Style

Beckett, R., Davies, S., & Mortlock, A. (1992). ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3]. TETRAHEDRON-ASYMMETRY, 3(1), 123–136.

MLA Style

Beckett, R, et al. “ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3].” TETRAHEDRON-ASYMMETRY, vol. 3, no. 1, 1992, pp. 123–36.

Chicago Style

Beckett, R, S Davies, and A Mortlock. 1992. “ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3].” TETRAHEDRON-ASYMMETRY 3 (1): 123–36.
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Publisher copy:: 10.1016/S0957-4166(00)82319-8

Authors

+ Beckett, R More by this author

Role:: Author

+ Davies, S More by this author

Role:: Author

+ Mortlock, A More by this author

Role:: Author

Journal:: TETRAHEDRON-ASYMMETRY More from this journal
Volume:: 3
Issue:: 1
Pages:: 123-136
Publication date:: 1992-01-01
DOI:: 10.1016/S0957-4166(00)82319-8
EISSN:: 1362-511X
ISSN:: 0957-4166

Language:: English
Pubs id:: pubs:168596
UUID:: uuid:e466f0cc-a92e-4373-9901-42985310f9d1
Local pid:: pubs:168596
Source identifiers:: 168596
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_e466f0cca92e4373990142985310f9d1

Terms of use

Copyright date:: 1992

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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