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Volumn 64, Issue 7, 2008, Pages 1409-1419

Diastereoselective borono-Mannich reactions on cyclic N-acyliminium ions

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 METHOXYBENZYL 6 BENZOFURAN 2 YL) 5 HYDROXYPIPERIDIN 2 ONE; 1 (4 METHOXYBENZYL) 5 HYDROXY 6 STYRYLPIPERIDIN 2 ONE; 1 (4 METHOXYBENZYL) 5 METHOXY 6 STYRYLPIPERIDIN 2 ONE; 1 (4 METHOXYBENZYL) 5,6 DIHYDROXYPIPERIDIN 2 ONE; 1 (4 METHOXYBENZYL) 6 (FURAN 2 YL) 5 HYDROXYPIPERIDIN 2 ONE; 1 (4 METHOXYBENZYL) 6 HYDROXY 5 METHOXYPIPERIDIN 2 ONE; 1 (4 METHOXYBENZYL) 6 STYRYLPIPERIDIN 2,5 DIONE; 1 BENZL 4 HYDROXY 5 STYRYLPYRROLIDIN 2 ONE; 1 BENZYL 4 (BENZYLOXY) 5 (2 THIENYL) PYRROLIDIN 2 ONE; 1 BENZYL 4 (BENZYLOXY) 5 (3,4 DIMETHOXYPHENYL)PYRROLIDIN 2 ONE; 1 BENZYL 4 (BENZYLOXY) 5 (4 METHOXYPHENYL)PYRROLIDIN 2 ONE; 1 BENZYL 4 (BENZYLOXY) 5 (FURAN 2 YL) PYRROLDIN 2 ONE; 1 BENZYL 4 (BENZYLOXY) 5 HYDROXY 5 STYRYLPYRROLIDIN 2 ONE; 1 BENZYL 4 (BENZYLOXY) 5 PHENETHYLPYRROLIDIN 2 ONE; 1 BENZYL 4 (BENZYLOXY) 5 STYRYKPYRROLIDIN 2 ONE; 1 BENZYL 4 HYDROXY 5 STYRYLPYRROLIDIN 2 ONE; 1 BENZYL 4,5 DIHYDROXYPYRROLIDIN 2 ONE; 1 BENZYL 5 (3,4 DIMETHOXYPHENYL) 4 HYDROXYPYRROLIDIN 2 ONE; 1 BENZYL 5 (FURAN 2 YL) 4 HYDROXYPYRROLIDIN 2 ONE; 1 BENZYL 5 STYRYL HEXAHYDROBOROLO[3,4 B]PYRROL 2 (1H) ONE; 2 BENZYL 6 OXA 2 AZA BICYCLO[3.1.0] HEXAN 3 ONE; 5 (BENZOFURAN 2 YL) 1 BENZYL 4 (BENZYLOXY) PYRROLDIN 2 ONE; 5 (BENZOFURAN 2 YL) 1 BENZYL 4 HYDROXYPYRROLIDIN 2 ONE; BORONIC ACID DERIVATIVE; IMINE; INDOLIZIDINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 37649007817     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.11.046     Document Type: Article
Times cited : (41)

References (46)
  • 27
    • 37649002687 scopus 로고    scopus 로고
    • note
    • The addition of allyltrimethylsilane or tributylstannane to five- and six-membered ring N-acyliminium ions derived from precursors C or D (Scheme 1), gives product mixtures that favour the cis isomer, however, this selectivity is only modest. For five-membered ring examples see Refs. 2a (cis/trans=77:23), 2b (cis/trans=80:20), 2f (cis/trans=83:17), 2g (cis/trans 83:17), 2h (cis/trans=66:34), 2i (cis/trans=80:20) and 2l (cis/trans=57:43). For six-membered ring examples see Refs. 2l (cis/trans=76:24) and 2o (cis/trans=63:27). For the cis-selective allylation (cis/trans=77:23) of the O-TBS, methylcarbamate analogue of 1 (n=1, Scheme 2) see Ref. 2a.
  • 28
    • 37649023454 scopus 로고    scopus 로고
    • For the synthesis of cis-adducts from aryl or alkynyl migration from a C-3 silyl ether to C-2 iminium ion see:
  • 36
    • 37649000806 scopus 로고    scopus 로고
    • Hall D.G. (Ed), Wiley VCH, Weinheim Chapter 7
    • Batey R.A. In: Hall D.G. (Ed). Boronic Acids (2005), Wiley VCH, Weinheim 279-304 Chapter 7
    • (2005) Boronic Acids , pp. 279-304
    • Batey, R.A.1
  • 39
    • 37649022506 scopus 로고    scopus 로고
    • note
    • 2o
  • 41
    • 37649000669 scopus 로고    scopus 로고
    • 4,5 for its C-5 epimer (see (b) below) from NMR analysis of a mixture of 11 and its C-5 epimer was difficult and therefore we are not 100% confident of the stereochemistry at C-5 in 11.
  • 42
    • 37649014234 scopus 로고    scopus 로고
    • f value) than the mixture of 11 and 5-epi-11, again consistent with the epoxide structure for 13.
  • 43
    • 37649021954 scopus 로고    scopus 로고
    • note
    • Prepared according to Ref. 2r and references cited therein.
  • 44
    • 33947701099 scopus 로고    scopus 로고
    • For a review on trifluoroborate salt chemistry see:
    • For a review on trifluoroborate salt chemistry see:. Stefani H.A., Cella A.S., and Vieira A.S. Tetrahedron 63 (2007) 3623-3658
    • (2007) Tetrahedron , vol.63 , pp. 3623-3658
    • Stefani, H.A.1    Cella, A.S.2    Vieira, A.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.