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Volumn 33, Issue 4, 1992, Pages 455-456

Regioselective [3 + 2] annulations with rhodium(ii)-stabilized vinylcarbenoids

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0026544033 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)93966-2 Document Type: Article

Times cited : (20)

References (17)

1
- 0001651926
- For a detailed account of the various 3 + 2 annulation procedures that have been developed, see, and references cited therein.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 6691
- Hudlicky¹ Fleming² Radesca³

2
- 0025145651
- For previous examples of 3 + 2 annulations using Fisher vinylcarbene complexes or free vinylcarbenes, see
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 5660
- Murray¹ Yang² Wulff³

3
- 8944245581
- Zur Bildung von Vinylcyclopropan- und Cyclopentenderivaten aus alkenylsubstituierten Chromcarben-Komplexen: Konkurrenz von formalen [2 + 1]- und [3 + 2]-Cycloadditionen
- (1991) Chemische Berichte , vol.124 , pp. 957
- Wienand¹ Reissig²

4
- 0000616107
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6695
- Boger¹ Brotherton²

5
- 0001405856
- and references cited therein.
- (1991) J. Org. Chem. , vol.56 , pp. 3817
- Davies¹ Clark² Smith³

6
- 0001739961
- (1985) Org. React. , vol.33 , pp. 247
- Hudlicky¹ Kutchan² Naqvi³

7
- 0001471943
- (1989) Tetrahedron Lett. , vol.30 , pp. 5057
- Davies¹ Clark² Church³

8
- 84918667222
- 1% of catalyst was used in all the carbenoid reactions except for the conversion of 3 to 11 (5 % catalyst).

9
- 84918662231
- The stereochemistry of the cyclopropanes was based on distinctive nOe enhancements, coupling constants and chemical shifts. For related systems, see Refs 2a,b and 5.

10
- 0001796781
- Donor-acceptor-substituted cyclopropanes: Versatile building blocks in organic synthesis
- (1988) Topics Curr. Chem. , vol.144 , pp. 73
- Reissig¹

13
- 84918701583
- The stereochemistry of 6c was based on the observation of a strong noe enhancement between the methine protons and a lack of an enhancement between the methyl group and the methine proton adjacent to the ethoxy group.

15
- 84918680638
- Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem., in press.

16
- 0025358489
- BHT esters have been used previously in carbenoid reactions to enhance anti selectivity in cyclopropanations with diazoacetates., See
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 1906
- Doyle¹ Bagheri² Wandless³ Harn⁴ Brinker⁵ Eagle⁶ Loh⁷

17
- 85008090337
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 726
- Evans¹ Woerpel² Hinman³ Faul⁴

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