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Volumn 50, Issue 3, 2011, Pages 688-691

Iridium-catalyzed asymmetric intramolecular allylic amidation: Enantioselective synthesis of chiral tetrahydroisoquinolines and saturated nitrogen heterocycles

Author keywords

allylic compounds; asymmetric catalysis; iridium; nitrogen heterocycles; phosphoramidites

Indexed keywords

ALLYLIC COMPOUNDS; AMIDATION; ASYMMETRIC CATALYSIS; BIOLOGICALLY ACTIVE COMPOUNDS; CHIRAL BUILDING BLOCKS; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY; IRIDIUM CATALYSIS; NITROGEN HETEROCYCLES; PHOSPHORAMIDITES; TETRAHYDROISOQUINOLINES;

EID: 78651395120     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006039     Document Type: Article
Times cited : (64)

References (49)
  • 8
    • 0142123967 scopus 로고    scopus 로고
    • For a single example of palladium-catalyzed allylic amidation with 88 % ee, see.
    • For a single example of palladium-catalyzed allylic amidation with 88 % ee, see:, K. Ito, S. Akashi, B. Saito, T. Katsuki, Synlett 2003, 1809.
    • (2003) Synlett , pp. 1809
    • Ito, K.1    Akashi, S.2    Saito, B.3    Katsuki, T.4
  • 37
    • 78651405629 scopus 로고    scopus 로고
    • our case this is a Stille reaction with tributylstannylpropenol, see the Supporting Information for details.
    • In our case this is a Stille reaction with tributylstannylpropenol, see the Supporting Information for details.
  • 38
    • 78651395051 scopus 로고    scopus 로고
    • This is a major advantage over N-protecting groups, which have to be removed by hydrogenolysis.
    • This is a major advantage over N-protecting groups, which have to be removed by hydrogenolysis.
  • 39
    • 78651389419 scopus 로고    scopus 로고
    • The 6,7-dimethoxy substitution pattern is part of a large number of tetrahydroisoquinoline compounds with biological activity. Hence, we chose this substrate as the starting point of our studies.
    • The 6,7-dimethoxy substitution pattern is part of a large number of tetrahydroisoquinoline compounds with biological activity. Hence, we chose this substrate as the starting point of our studies.
  • 40
    • 78651388369 scopus 로고    scopus 로고
    • With catalytic amounts of DBU the same enantioselectivity was found, however the reactions did not result in full conversion. The role of the base has to be elucidated further.
    • With catalytic amounts of DBU the same enantioselectivity was found, however the reactions did not result in full conversion. The role of the base has to be elucidated further.
  • 46
    • 78651393012 scopus 로고    scopus 로고
    • The reactions were scaled up to 1.0 mmol and gave the same results in terms of yields and enantioselectivities.
    • The reactions were scaled up to 1.0 mmol and gave the same results in terms of yields and enantioselectivities.
  • 47
    • 78651385310 scopus 로고    scopus 로고
    • The absolute configuration of the products was determined by comparison of the optical rotation of compound 2 with the literature value (Ref. [8]). The absolute configuration of the other products was assigned by analogy.
    • The absolute configuration of the products was determined by comparison of the optical rotation of compound 2 with the literature value (Ref. [8]). The absolute configuration of the other products was assigned by analogy.
  • 48
    • 78651412302 scopus 로고    scopus 로고
    • the absence of the Ir catalyst, no reaction was observed, thus indicating that the Ir catalyst is essential for this transformation to take place.
    • In the absence of the Ir catalyst, no reaction was observed, thus indicating that the Ir catalyst is essential for this transformation to take place.
  • 49
    • 78651412136 scopus 로고    scopus 로고
    • For a discussion of possible mechanisms for this transformation, see the Supporting Information.
    • For a discussion of possible mechanisms for this transformation, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.