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Volumn 15, Issue 16, 2009, Pages 4088-4101

Highly enantioselective synthesis of β-aminophosphinates with two stereogenic atoms and their conversion into optically pure ethyl β-amino-H-phosphinates

Author keywords

Aminophosphinates; Cram's rules; Enanliosclectivity; Phosphorus; Synthetic methods

Indexed keywords

AMINOPHOSPHINATES; CRAM'S RULES; DIASTEREOISOMERS; ENANLIOSCLECTIVITY; ENANTIO-SELECTIVE SYNTHESIS; ENANTIOSELECTIVE FORMATIONS; INDUCED ACTIVITIES; NUCLEOPHILIC ATTACKS; PHOSPHINATES; PHOSPHORUS ATOMS; PROTECTING GROUPS; SYNTHETIC METHODS;

EID: 65349130021     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802248     Document Type: Article
Times cited : (19)

References (62)
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    • 1HNMR spectroscopic data, see the supporting information; CCDC-693686 (41) and CCDC-693685 (4 c') contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
    • 1HNMR spectroscopic data, see the supporting information; CCDC-693686 (41) and CCDC-693685 (4 c') contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
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    • It should be pointed out that it is difficult to synthesize the racemic 61and 61′with an Sconfiguration at the S atom, and the racemates that involve four isomers were prepared by racemic N-tert-butane-sulfinylimines; therefore, it is necessary for us to eliminate the chir-ality of the S atom and HPLC only became possible with the above treatment
    • It should be pointed out that it is difficult to synthesize the racemic 61and 61′with an Sconfiguration at the S atom, and the racemates that involve four isomers were prepared by racemic N-tert-butane-sulfinylimines; therefore, it is necessary for us to eliminate the chir-ality of the S atom and HPLC only became possible with the above treatment.
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    • 4 plays in this reaction. Possibly, this reagent activates PhSH and accelerate the reaction, which is now under investigation and our results will be reported in the future elsewhere.
    • 4 plays in this reaction. Possibly, this reagent activates PhSH and accelerate the reaction, which is now under investigation and our results will be reported in the future elsewhere.
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    • It should be pointed out that CF3SO3H is usually used as an extremely effective desulfonylation agent for more details, see: P. Sun, S. M. Weinreb, J. Org. Chem. 1997, 62, 8604-8608, however, it is strange that when this agent was applied to our substrates, desul-fonylamination took place, and we only obtained the alkene. This outcome is another reason why we chose the tcrf-butylsulfinylamine-protected substrate for further study: indeed, some β-tert-butylsulfo- nylamine-protected phosphinates demonstrated the tendency to form alkenes under acidic conditions, for example
    • 3H is usually used as an extremely effective desulfonylation agent (for more details, see: P. Sun, S. M. Weinreb, J. Org. Chem. 1997, 62, 8604-8608); however, it is strange that when this agent was applied to our substrates, desul-fonylamination took place, and we only obtained the alkene. This outcome is another reason why we chose the tcrf-butylsulfinylamine-protected substrate for further study: indeed, some β-tert-butylsulfo- nylamine-protected phosphinates demonstrated the tendency to form alkenes under acidic conditions, for example:
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    • For the ORTEP drawings of the two compounds, refer to ref. [14].
    • For the ORTEP drawings of the two compounds, refer to ref. [14].
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.