Preparation of Optically Active New Mercapto Chiral Auxiliaries Derived From Camphor

Lee, Dong‐Sheng; Hung, Shung-Ming; Lai, Ming-Chun; Chu, Han-Yang; Yang, Teng‐Kuei

doi:10.1080/00304949309356263

Cited by 16 publications

(1 citation statement)

References 16 publications

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“…Synthesis of Ylide Precursors 3a, 3b, 4a, 4b, 6a, 6b, 7a, and 7b. Since the appearance of chiral sulfides 2 , 3 , and 5 derived from d -(+)-camphor ( 1 ), an easily available chiral pool, in 1988, they have found several applications in asymmetric synthesis and reactions . In some cases, satisfactory results could be achieved.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Enantiomerically Enriched (2R,3R)- or (2S,3S)-trans-2,3-Diaryloxiranes via Camphor-Derived Sulfonium Ylides

et al. 1996

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Easily available D-(+)-camphor-derived sulfides 3, 4, 6, and 7 were employed for enantioselective epoxidation via an ylide route. When benzylated or methylated sulfides were used as reagents or mediators for benzylidene transfer, stoichiometric and catalytic epoxidations were realized, respectively. Opposite asymmetric induction was achieved only when sulfides containing exo- (3 and 4) and endo- (6 and 7) alkylthio groups were used. That is, both (+)- and (-)-trans-diaryloxiranes could be obtained in excellent yields and moderate to good ee values under extremely mild conditions from the same chiral pool-derived reagents. A nonbonded interaction between the free OH in the ylides from sulfides (3, 6, and 7) and the carbonyl group of aldehydes controls the approach of the substrates to the ylidic carbon preferentially at one specified face and therefore leads to a more efficient asymmetric induction than that in the case of the ylide from methyl-protected hydroxylated sulfides 4, which cannot cause such an interaction. The same opposite asymmetric induction was also observed in the catalytic reaction with methyl-protected hydroxylated sulfide 4b and unprotected hydroxylated sulfide 3b.

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Section: Resultsmentioning

confidence: 99%

Preparation of Enantiomerically Enriched (2R,3R)- or (2S,3S)-trans-2,3-Diaryloxiranes via Camphor-Derived Sulfonium Ylides

et al. 1996

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ChemInform Abstract: Preparation of Optically Active New Mercapto Chiral Auxiliaries Derived from Camphor.

et al. 1994

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Catalytic asymmetric borane reduction of prochiral ketones using chiral camphor‐derived mercapto‐alcohols

1998

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CommunicationCatalytic asymmetric borane reduction of prochiral ketones using chiral camphor-derived mercapto-alcohols ZHOU, Yong-Gui(FgJ;rkB) HOU, Xue-Long(#%%)' DAI, Li-Xin (a3m) Abstract Easily available D-(+)-camphor-derived chiral mercapt*alcohols 2 and 3 were employed for catalytic asymmetric borane reduction of aromatic ketones. Moderate enantioselectivities with e.e. 20.2-72.1% were obtained with 10 mol% catalyst. Opposite asymmetric induction was achieved' when mercaptc-alcohols 2 and 3 were used.

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Preparation of Optically Active New Mercapto Chiral Auxiliaries Derived From Camphor

Cited by 16 publications

References 16 publications

Preparation of Enantiomerically Enriched (2R,3R)- or (2S,3S)-trans-2,3-Diaryloxiranes via Camphor-Derived Sulfonium Ylides

Preparation of Enantiomerically Enriched (2R,3R)- or (2S,3S)-trans-2,3-Diaryloxiranes via Camphor-Derived Sulfonium Ylides

ChemInform Abstract: Preparation of Optically Active New Mercapto Chiral Auxiliaries Derived from Camphor.

Catalytic asymmetric borane reduction of prochiral ketones using chiral camphor‐derived mercapto‐alcohols

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