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Volumn 59, Issue 19, 2003, Pages 3527-3536

A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries

Author keywords

(S) pyroglutamic acid; Allyltributyltin; Asymmetric addition; Chiral auxiliary; Indole alkaloid; Silyl enol ether; carboline

Indexed keywords

ALLYL COMPOUND; ALLYL TRIBUTYLTIN; CARBOLINE DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; SILANE DERIVATIVE; SILYL ETHER; UNCLASSIFIED DRUG;

EID: 0037420873     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00420-4     Document Type: Article
Times cited : (27)

References (38)
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  • 21
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    • For instance, the addition of (S)-alanine derivatives to N-9 position of β-carboline resulted in the formation of 9-alanyl derivatives in yields below 20% under standard conditions
    • For instance, the addition of (S)-alanine derivatives to N-9 position of β-carboline resulted in the formation of 9-alanyl derivatives in yields below 20% under standard conditions.
  • 28
    • 0004082390 scopus 로고
    • Silyl enol ethers were synthesized according to the reported method, see: San Diego: Academic. pp 99-105, and references cited therein
    • Silyl enol ethers were synthesized according to the reported method, see: Colvin E.W. Silicon Reagents in Organic Synthesis. 1988;Academic, San Diego. pp 99-105, and references cited therein.
    • (1988) Silicon Reagents in Organic Synthesis
    • Colvin, E.W.1
  • 29
    • 85031185862 scopus 로고    scopus 로고
    • In the previous reaction which adopted N-phenylsulfonylprolinyl group as a chiral auxiliary, addition using silyl enol ethers afforded the products in good yields but poor diastereoselectivity (<20%)
    • In the previous reaction which adopted N-phenylsulfonylprolinyl group as a chiral auxiliary, addition using silyl enol ethers afforded the products in good yields but poor diastereoselectivity (<20%).
  • 32
    • 0032805195 scopus 로고    scopus 로고
    • The coordination mechanism was supposed to participate only in the reaction of β-carbolines which have two carbonyl and/or sulfonyl oxygens at the reaction sites. In the cases of isoquinoline derivatives, only the steric factor might control the stereochemistry; see (a) Itoh T., Nagata K., Miyazaki M., Ohsawa A. Synlett. 1999;1154 (b) Itoh T., Nagata K., Miyazaki M., Kameoka K., Ohsawa A. Tetrahedron. 57:2001;8827 (c) Nagata K., Itoh T., Kameoka K., Miyazaki M., Ohsawa A. Heterocycles. 55:2001;2269.
    • (1999) Synlett , pp. 1154
    • Itoh, T.1    Nagata, K.2    Miyazaki, M.3    Ohsawa, A.4
  • 33
    • 0035887534 scopus 로고    scopus 로고
    • The coordination mechanism was supposed to participate only in the reaction of β-carbolines which have two carbonyl and/or sulfonyl oxygens at the reaction sites. In the cases of isoquinoline derivatives, only the steric factor might control the stereochemistry; see (a) Itoh T., Nagata K., Miyazaki M., Ohsawa A. Synlett. 1999;1154 (b) Itoh T., Nagata K., Miyazaki M., Kameoka K., Ohsawa A. Tetrahedron. 57:2001;8827 (c) Nagata K., Itoh T., Kameoka K., Miyazaki M., Ohsawa A. Heterocycles. 55:2001;2269.
    • (2001) Tetrahedron , vol.57 , pp. 8827
    • Itoh, T.1    Nagata, K.2    Miyazaki, M.3    Kameoka, K.4    Ohsawa, A.5
  • 34
    • 0035697176 scopus 로고    scopus 로고
    • The coordination mechanism was supposed to participate only in the reaction of β-carbolines which have two carbonyl and/or sulfonyl oxygens at the reaction sites. In the cases of isoquinoline derivatives, only the steric factor might control the stereochemistry; see (a)
    • The coordination mechanism was supposed to participate only in the reaction of β-carbolines which have two carbonyl and/or sulfonyl oxygens at the reaction sites. In the cases of isoquinoline derivatives, only the steric factor might control the stereochemistry; see (a) Itoh T., Nagata K., Miyazaki M., Ohsawa A. Synlett. 1999;1154 (b) Itoh T., Nagata K., Miyazaki M., Kameoka K., Ohsawa A. Tetrahedron. 57:2001;8827 (c) Nagata K., Itoh T., Kameoka K., Miyazaki M., Ohsawa A. Heterocycles. 55:2001;2269.
    • (2001) Heterocycles , vol.55 , pp. 2269
    • Nagata, K.1    Itoh, T.2    Kameoka, K.3    Miyazaki, M.4    Ohsawa, A.5
  • 35
    • 85031183069 scopus 로고    scopus 로고
    • When 3 equiv. of HMPA was added to the reaction shown in entry 6 of Table 3, the ee was lowered to 50%
    • When 3 equiv. of HMPA was added to the reaction shown in entry 6 of Table 3, the ee was lowered to 50%.
  • 36
    • 0037159696 scopus 로고    scopus 로고
    • Enantioselective synthesis of an alkaloid and an alkaloid derivative was carried out using the product described in the present paper, see:
    • Enantioselective synthesis of an alkaloid and an alkaloid derivative was carried out using the product described in the present paper, see: Itoh T., Miyazaki M., Nagata K., Yokoya M., Nakamura S., Ohsawa A. Heterocycles. 58:2002;115.
    • (2002) Heterocycles , vol.58 , pp. 115
    • Itoh, T.1    Miyazaki, M.2    Nagata, K.3    Yokoya, M.4    Nakamura, S.5    Ohsawa, A.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.